We always remember the great upsets and Cinderellas of the NCAA Tournament, but what about the teams that fell just short of shocking the world? Here's a list of the 31 most notable examples of valiant but futile attempts at first round upsets.
1) #16 Princeton vs. #1 Georgetown, 1989
When Maryland-Baltimore County finally became the first 16 seed to upset a top seed (Virginia) in the 2018 NCAA Tournament, all college basketball junkies knew the clip that was going to be played to commemorate the event. Princeton alumni and fans probably know it by heart. Kirk Mueller, a sophomore center, his lip still swollen from getting an elbow from his Georgetown counterpart, Alonzo Mourning, earlier in the game, putting up a final potential game-winning shot at the buzzer, blocked (some would say while being fouled) by Mourning. "The Hoyas escape, and I mean escape" was the final call from Billy Packer, and for good reason. Coming into the tournament that year there had been talk of eliminating the automatic bid for small conferences, but this game may have single-handedly saved it for the next 30 years and counting. It received a large amount of pregame hype for what many considered to be a sure blow-out, including a young ESPN analyst named Dick Vitale who promised to don a cheerleader outfit and serve as a ball boy for Princeton in their second round game if they pulled off the upset (unless you're a Georgetown fan, missing out on that visual was probably the only upside to Princeton not pulling off the upset). Utilizing coach Pete Carrill's "Princeton" offense and possessing the nation's best defense, the Tigers took a shocking 29-21 lead at halftime. Even in the era before cell phones and Twitter, word spread fast and TV sets around the country tuned in en masse for the second frame. Georgetown stormed back, and took the lead 50-49 when Mourning hit one of two free throw attempts with 18 seconds remaining. Mourning then blocked not one, but two potential game winners in the waning moments, knocking one out of bounds at the six second mark which set up Mueller's final attempt (you can watch the entire sequence here). After the game, Georgetown coach John Thompson remarked "it's an understatement to say that Princeton deserved to win." Agreed. But in the process, they inspired countless generations of little guys with slingshots, up to and including the UMBC Retrievers.
2) #16 East Tennessee State vs. #1 Oklahoma, 1989
The Princeton-Georgetown game so dominated the narrative of the 1989 NCAA Tournament, both at the time and in retrospect, that most have forgotten that another #16 seed almost pulled off the improbable that same weekend. From the time the NCAA expanded to 64 teams in 1985 to UMBC upsetting Virginia in 2018, a #16 seed came within a basket of winning just four times, and two of those came in 1989. Perhaps most amazing for East Tennessee State is that unlike Princeton, they actually led by a wide margin for much of the game, including by as much as 17 points in the first half. The Sooners, defending National runners-up and led by star point guard Mookie Blaylock, methodically chipped away at the lead in the second half, as East Tenneessee State went ice cold from the field. When Blaylock hit a driving lay-up to give Oklahoma a 72-71 lead with 1:21 left, it was only their second lead of the game and it turned out to be the final score, as both squads struggled to connect down the stretch, and a final half-court heave from Alvin West couldn't find net (someone put the entire game on YouTube, if you're inclined to watch). Oklahoma was eventually upset in the Regional Semifinals by #5 seed Virginia, while the Buccaneers made their mark three years later as a #14 seed, upsetting Arizona in the first round of the 1992 tournament. In addition to Georgetown and Oklahoma, top seeded Illinois also struggled on that fateful Thursday in March, holding on for a six-point victory over #16 seed McNeese State.
3) #15 Georgia Southern vs. #2 Syracuse, 1987
Not much was expected of Syracuse in '86-'87 after their star guard Pearl Washington had left early for the NBA. But sparked by Sherman Douglas and freshman sensation Derrick Coleman, the Orange grinded out a surprise 31-7 record and a #2 seed in the NCAA Tournament. As luck would have it, their home base, the Carrier Dome, was hosting tournament games that season, and few foresaw the Orange struggling in the first two rounds in literal home games. Their first opponent, Georgia Southern, were unexpected champions of the Atlantic Sun conference and playing in just their second NCAA Tournament game in school history. But the Eagles from tiny Statesboro, GA would not go quietly, leading 40-39 at halftime and continually coming from behind in the second half when the Orange tried to put the game away. Senior guard Greg Monroe (no relation to the future Georgetown and Pistons star) was finally able to seal it with a series of clutch three-pointers and Syracuse moved on, 79-73. Locked in after the near-upset, the Orange made it all the way to their first National Final appearance, losing to Indiana on Keith Smart's dramatic game winner. Georgia Southern has returned to the tournament just once since, a blowout first round loss as a #15 seed in 1992.
4) #12 UW-Milwaukee vs. #5 Notre Dame, 2003
The 12-over-5 upset has become so prevalent annually in the NCAA Tournament that even the most novice of bracket prognosticators knows to pick at least one in their office pool entry. Occasionally that can work against you, when a highly-touted #12 seed comes up just short, as was the case with Wisconsin-Milwaukee in 2003. Coached by Bruce Pearl, the Panthers were making their first tournament appearance in school history, but many had them pegged as a prime upset opportunity against a vulnerable-looking squad from Notre Dame. Things looked especially dire for the Irish when their star forward Matt Carroll left late in the first half with an apparent sprained ankle. But they still had point guard Chris Thomas, who led all scorers with 27 points, and freshman power forward Torin Francis, who hit the eventual game winner on a put-back with 32 seconds left. Trailing by one, Milwaukee's best player, Clay Tucker (who has enjoyed a long pro career in Europe), had the ball in his hands at the end, but when he was triple-teamed driving to the hoop he dished to open teammate Dylan Page, who couldn't put in a jump hook at the buzzer. Carroll returned from his injury in the second round for Notre Dame, who managed to reach the Sweet 16. Milwaukee returned to the tournament as a #12 seed in 2005 and on the second try pulled off the vaunted upset over Alabama.
5) #14 Pepperdine vs. #3 Michigan, 1994
Though Michigan's Fab Five officially ceased to be following the 1993 NCAA Championship Game, when Chris Webber declared early for the NBA draft, the Wolverines were still a dangerous team in '93-'94. The roster featured the other four members of the highly touted 1991 recruiting class: Juwan Howard, Jalen Rose, Jimmy King, and Ray Jackson, now all juniors. Entering the NCAA Tournament as a #3 seed, they were determined to prove themselves a viable Final Four threat even without Webber, and were eventually were able to do so, but not until surviving a scare from Pepperdine. A mid-sized, scenic, private school located in the hills of Malibu, the Waves had become a perennial tournament fixture in the '80s and early '90s under coaches Jim Harrick and Tom Asbury, but were looking for their first postseason victory in 12 years. When the two teams locked up in Wichita, Michigan led for much of the way but the game, and the crowd, turned against the Wolverines when Howard committed a hard foul with a subsequent stare-down of Damin Lopez, Pepperdine's diminutive point guard. Seemingly inspired by the taunt, Lopez heated up down the stretch, hitting five three-pointers in the second half. He had a chance to win the game in regulation, but his last second shot was blocked by Rose. Michigan played strong in overtime, hitting all ten of their free throws to pull away for a 78-74 win. After further close wins over Texas and Maryland, Michigan lost in the Regional Finals against the eventual national champs from Arkansas. Pepperdine finally won a tournament game in 2000, upsetting Bob Knight's Indiana as a #11 seed.
6) #15 Robert Morris vs. #2 Villanova, 2010
The tournament had been nine years removed from a 15 seed upsetting a 2 seed when Robert Morris took the floor against Villanova on the opening Thursday of its 2010 edition. The Wildcats were obviously heavily favored, having reached the 2009 Final Four, but their confidence was slightly tempered before tip-off when it was announced that back court starters Scottie Reynolds and Corey Fisher were being benched for an apparent off-court infraction. Though coach Jay Wright called it a "teaching point," neither benching lasted long, but Reynolds struggled to find his rhythm, possibly as a result. With just over four minutes to play in the game, the star shooting guard was just 2-of-15 from the floor, and Robert Morris held a 55-47 lead. Galvanized by the performance of their own star guard, Karon Abraham, the Colonials seemed primed to join Hampton, Coppin State, Richmond, and Santa Clara in the hallowed annals of #15 seed victors. But then Reynolds did something all great players should do when struggling to shoot: he got himself to the free throw line, hitting 15-of-16 from the charity stripe to help lead the Wildcats back and send the game to overtime. Villanova then hung on for dear life in the extra period, ultimately winning the game 73-70 when Robert Morris' Meize Nwigwe was errant on a desperation three-pointer. It probably wasn't the lesson Wright intended to "teach" Reynolds, but it all worked out, at least for one night. Two days later Villanova was ousted by #10 seed Saint Mary's.
7) #13 La Salle vs. #4 Seton Hall, 1992
Seton Hall had a perfectly fine season in '91-'92, though it didn't quite live up to expectations. Returning their best player, Terry Dehere, from a team that won the Big East and reached the Elite Eight in 1991, they were upset in the semifinals of the 1992 Big East Tournament and entered the NCAA Tournament as a #4 seed. Their first round opponent was La Salle, soon to be an Atlantic-10 member, but then the champions in their final season in the MAAC. The Explorers were no stranger to March pressure, playing in their fourth tournament in five years under coach Speedy Morris. Their star player Randy Woods averaged 27.3 points per game and didn't disappoint against the Pirates, netting 21 points in the first half and staking La Salle to an early lead. Trailing by eight with just 4:12 left on the clock, Seton Hall was finally able to muster a comeback thanks to John Leahy, who scored nine straight points himself down the stretch, and set up the game-winning shot by Dehere. Like many Cinderella hopefuls, La Salle lived and died by the three-pointer, and struggled down the stretch to finish just 9-of-30 for the game. The Explorers would not return to the NCAA Tournament again until 2013, when this time as a #13 seed they pulled off two upsets and reached the Sweet 16.
8) #15 Texas Southern vs. #2 Arkansas, 1995
Coming into the 1995 tournament, Texas Southern was no stranger to being a #15 seed taking on a traditional power in the first round. The year prior they had taken on Grant Hill and Duke, putting up a fight but losing 82-70. Duke went on to reach the National Final and lose to Arkansas, who was Texas Southern's first round opponent in 1995, and also a team they were already familiar with. That wasn't necessarily a good thing in this case, as the Razorbacks had defeated the Tigers during the '93-'94 regular season by 66 points. The story line was different this time, even after Arkansas opened an early 17-point lead. Texas Southern fought back to take a lead early in the second half, then fell behind again by 10 before mounting a final comeback. After Corliss Williamson gave the Razorbacks a 79-76 lead with 27 seconds left, Texas Southern's Randy Bolden had to chance to essentially live out a childhood driveway hoop dream. He was fouled while shooting a three-pointer with 6.1 seconds left, and was granted a trio of free throws to tie the game. The team's best free throw shooter, at 80%, Bolden hit the first two, but was short on the third, allowing Arkansas to escape. The immediacy of the close call wasn't lost on their coach, Nolan Richardson, who chided his team after the game for their poor play. That coaching strategy seemed to work, as Arkansas won their next two games in overtime and eventually made it all the way back to the National Final, this time losing to UCLA. Texas Southern has made five more tournament appearances since 1995, but is still searching for their first postseason win.
9) #13 Pacific vs. #4 Boston College, 2006
Nobody wanted to draw Pacific in the 2006 NCAA Tournament. After upsetting Providence as a #12 seed in 2004 they followed it up with a first round win over Pittsburgh in 2005, and the senior-laden Tigers had cruised to a third straight Big West title to enter 2006 as a #13 seed. Boston College, considered a dark horse Final Four contender with their star upperclassmen Craig Smith and Jared Dudley, drew the unlucky straw. The game was played in Salt Lake City, closer to Pacific's home in Northern California, and the crowd was decidedly backing the underdog Tigers anyway. Pacific's star power forward Christian Maraker did not disappoint, finishing with 30 points and 9 rebounds, and hitting a clutch three-pointer that capped a 13-point comeback and sent the game to overtime. The extra period was back-and-forth, with a pair of free throws from Smith (who finished with 25 points and 13 rebounds) tying the game at the end of the first overtime after a controversial foul call against Maraker. Boston College proceeded to score the first nine points of second overtime and pulled away for an 88-76 win. The Eagles did reach the Sweet 16, where they lost to top seeded Villanova in overtime.
10) #12 Miami (OH) vs. #5 Maryland, 1985
After his untimely death that occurred before he ever played an NBA game, Len Bias has become something of a spectral presence whose NCAA career has only grown exponentially in awed stature, with tapes of his games at Maryland passed around like Grateful Dead bootlegs. Though the majority of Bias' greatest moments came in the regular season and ACC Tournament rather than the NCAA Tournament, one exception came in the first round in 1985, when the Terps were being tested by Miami (OH). The Redhawks had a superstar of their own, Ohio-bred Ron Harper, and he pushed Bias to the brink in this match-up. Harper finished the game with 26 points, Bias with 25, and both shot exceptionally well from the field throughout as they dueled. After coming back from an 11-point second half deficit, Miami sent the game to overtime at 59-59. They seemed primed to put the game away late in the extra period, when Harper threw down a posterizing dunk that not only gave Miami a three-point lead, but also put him at the line while fouling out Bias (just watch this highlight, if you're ever questioning just how good Harper was before injuries set in). Harper missed the free throw, and Maryland's Adrian Branch hit a jumper to cut the lead to one, then stole the ensuing inbounds pass and passed the ball to Jeff Adkins, who laid in the game winner. Maryland needed another comeback and another huge game from Bias to avoid an upset at the hands of Navy in the second round, and then eventually fell to #8 seed and eventual national champions Villanova in the Regional Semifinals. Harper and Miami returned to the 1986 tournament as a #10 seed, but fell just short again in another first round upset bid against Iowa State.
11) #12 St. Bonaventure vs. #5 Kentucky, 2000
When Kentucky lost in the first round of the NCAA Tournament to Marquette in 2008, it was their first such loss in 21 years. The closest they had come during that stretch to dropping a game so early in the big dance was this instance in 2000, when they were one year removed from winning the national championship. The Wildcats slumped in '99-'00, despite the presence of Jamaal Magloire and Tayshaun Prince, and came into the tournament looking like a prime upset victim as a #5 seed. Their first round opponent was St. Bonaventure, who was making their first tournament appearance in 22 years but was a solid defensive team with several upperclassmen, making them a dangerous early opponent. After falling behind by 13 points early in the second half, the Bonnies went on a 21-4 run to take the lead, with a Prince three-pointer eventually sending the game to overtime (St. Bonaventure guard Tim Winn had a chance to win it in regulation, but his coast-to-coast lay-up rimmed out at the buzzer). Already shorthanded due to a suspension of Desmond Allison for a DUI, Kentucky lost their starting point guard Saul Smith (coach Tubby's son) and backup center Jules Camara to injuries during the game, but still led for most of both overtimes. They had the game in hand late in the first extra period, but an inexplicable foul of St. Bonaventure guard David Capers allowed him to nail three free throws with 0.4 seconds left to send the game into a second overtime. The second overtime was close, but a missed three-pointer by Winn with three seconds left that could have tied the game allowed the Wildcats to ice the contest at the free throw line, 75-70. 12 years and three coaches later, St. Bonaventure finally returned to the tournament, but lost another close upset bid (see entry #25 below).
12) #15 Utah State vs. #2 Kansas, 2003
After finishing the season 25-7 and winning a difficult Big 12, Kansas assumed it deserved a #1 seed in a wide-open 2003 NCAA Tournament field. Feeling insulted by the #2 seed they received, the Jayhawks travelled to nearby Oklahoma City for what they expected to be a virtual tune-up against Utah State, but instead found themselves in a fire fight. Though Kansas never trailed in the game, they never built a comfortable lead either, often extending the lead to seven or eight points only for the Aggies to continually bring it back to one or two. Utah State senior forward Desmond Penigar led all players in scoring and rebounding, including what was ultimately the last basket of the game, a three-pointer that cut the lead to 64-61 with 47 seconds left. Penigar also had a chance to tie it after a Kansas turnover, but missed a three-pointer with just a few seconds remaining. Led by Nick Collison and Kirk Hinrich, Kansas cruised along past Arizona State, Duke, and Arizona en route to the Final Four, before losing to Carmelo Anthony and Syracuse in the Championship Game.
13) #15 Northern Arizona vs. #2 Cincinnati, 1998
Led by Ruben Patterson and Kenyon Martin, Cincinnati came into the 1998 tournament primed to atone from losing in a second round upset as a #3 seed the year prior. A postseason underachiever pall was starting to hang over Bob Huggins' program, and a first round match-up against a feisty Northern Arizona team playing closer to home in Boise looked like a dangerous proposition. The underdog Lumberjacks led the entire game until about the 16 minute mark of the second half, when the Bearcats took over the lead and held on the rest of the way. Cincinnati wisely avoided the trap that many high seeds fall into against smaller conference schools, and made full utilization of their size advantage. They pounded the ball inside, decimating the smaller Northern Arizona front line, getting them into early foul trouble and dominating the rebounding totals 41-26 (Martin grabbed 15 of them). D'Juan Baker hit the game winner for Cincinnati, a three-pointer with 3.6 seconds left to take a 65-62 lead, and Kawika Akina's desperation potentially tying heave for Northern Arizona clanged harmlessly off the rim. The Bearcats were upset in the next round anyway by West Virginia, and would return to the Sweet 16 just one more time under Huggins, in 2001. Northern Arizona has returned to the tournament just once time since this game, again as a #15 seed in 2000, and again putting a scare into their heavily favored opponent, St. John's.
14) #12 Iona vs. #5 Syracuse, 1998
It became a moot point when they won the 2003 championship, but for a long time Jim Boeheim's Syracuse teams had a reputation as an NCAA Tournament underachiever, despite Final Four appearances in 1987 and 1996. They suffered a historic first round upset against Richmond as a #2 seed in 1991, and had been additionally ousted by a lower seed in 1984, 1988, and 1990. After missing the tournament altogether in 1997, Syracuse entered the 1998 edition in the traditional land mine position of a #5 seed taking on a #12 seed. Even more intriguing was their opponent Iona being coached by former Boeheim assistant Tim Welsh, who had built a classic upset-minded roster, populated with a heavy dose of upperclassmen and outside shooters that had secured early season wins against Big East opponents Rutgers and Providence. The game was back-and-forth in the second half, with 10 lead changes over the final 10 minutes. The ninth lead change was Iona's John McDonald hitting a three-pointer with 24 seconds left to give his team a 61-60 advantage. On the ensuing possession, Syracuse's Todd Burgan took the ball inside, had his initial attempt blocked, recovered, and dished outside to a wide-open unlikely hero, Lithuanian Marius Janulis, who drained a three-pointer with 1.2 seconds on the clock. After Iona were unable to properly inbound to get off a final shot, the Orange breathed a heavy sigh of relief and moved on, eventually reaching the Sweet 16.
15) #15 East Tennessee State vs. #2 Wake Forest, 2003
16) #13 East Tennessee State vs. #4 Cincinnati, 2004
Under coaches Les Robinson and Alan LeForce, East Tennessee State was one of the nation's top mid-major programs in the late '80s and early '90s, producing some great tournament moments including a stunning upset of Arizona as a #14 seed in 1992. The program fell apart for a while, but returned to prominence under Ed DeChellis in '02-'03, winning the Southern Conference to secure a tournament bid as a #15 seed. Their first round opponent was Wake Forest, who was led by Josh Howard and enjoying their best season since Tim Duncan left for the NBA. Howard struggled offensively in this game, scoring just 12 points, but added some crucial shutdown defense and hit two clutch free throws that broke a 72-72 tie with 21 seconds left. Dynamic freshman point guard Tim Smith, who led all scorers in the game with 22, had a chance to tie the game for East Tennessee State at the buzzer, but missed a baseline three-pointer and Wake Forest escaped, 76-73. Smith was one of four starters that returned for East Tennessee State in '03-'04, and they were pegged as a leading Cinderella candidate heading into that tournament as a #13 seed. Trailing in their first round game late against Cincinnati, Smith, who was the game's leading scorer with 26, had a chance to cut Cincinnati's lead to one with 16 seconds left, but missed a driving lay-up and the Bearcats were able to run out the clock for an 80-77 win. Though Smith spent two more years at the school, and eventually won the conference Player of the Year award, he was unable to guide the Buccaneers back to the tournament.
17) #13 UC-Irvine vs. #4 Louisville, 2015
After waiting 40 years for their first NCAA Tournament appearance, the Anteaters of UC-Irvine made it count. Showing no signs of being rattled by matching up against a Rick Pitino-coached Louisville team just two years removed from being national champions, UC-Irvine leaned on their Senegalese sensation Mamdou N'Diaye, who was the tournament's tallest player at 7'6". Able to finish with dunks at the rim without even leaving his feet and swat away shot attempts with ease, N'Diaye electrified the Seattle crowd and finished the game with 12 points and five rebounds. It was a back-and-forth affair, with neither team ever leading by more than seven points, and with 43 seconds left Louisville's Wayne Blackshear made a courageous lay-up by going right at N'Diaye to tie the game at 55-55. After the Anteaters' Luke Nelson missed a three-pointer on the ensuing possession, the Cardinals iced it with a pair of free throws by Quentin Snider, then a steal in the closing seconds. Louisville eventually reached the Regional Finals before losing to Michigan State. Despite N'Diaye returning for his junior year, UC-Irvine failed to make the NCAA Tournament in 2016 after they were upset in the Big West Tournament semifinals.
18) #15 Winthrop vs. #2 Tennessee, 2006
Outside of Kentucky and Florida, the SEC has struggled immensely through the years in the NCAA Tournament, with its top teams often vulnerable to early upsets. Tennessee has been far from immune from that syndrome, and in 2006, when they were making their first return to the tournament in five years, many saw the Vols as over seeded and susceptible. They were done no favors by the selection committee, who matched up Tennessee against Winthrop, a well-coached (by Gregg Marshall, now the coach at Wichita State) and battle-tested team that was located close to the game site of Greensboro, NC. With multiple ties and lead changes, the game was a thrilling one until both offenses stalled late with the score tied 61-61. After multiple turnovers and difficult shots, Winthrop finally got a good look from Craig Bradshaw with 38 seconds left, but his three-pointer was errant, setting up Tennessee's final play. First year coach Bruce Pearl (who knew a thing or two about near-upsets from the other side, see #4 above) drew up the inbounds play for C.J. Watson, but it ended up in the hands of Chris Lofton, who drilled a three-pointer with 0.4 seconds left to finish the game (you can watch it here). Lofton's teammates mobbed him in celebration, and it would be Tennessee's only jubilation that March, as they were upset by #7 seed Wichita State in the next round. Winthrop returned to the tournament in 2007 as a #11 seed, and after seven previous unsuccessful attempts, finally won the first tournament game in school history, an upset over Notre Dame.
19) #14 Southern Utah vs. #3 Boston College, 2001
Southern Utah has been a Division I team for 30 years and counting but have made just one NCAA Tournament appearance in that time. And though they may have lost that one game, they sure did make it interesting. Surprise champions in 2001 of the now-defunct Mid-Continent Conference, the Thunderbirds were hardly a chic upset pick heading into the big dance as a #14 seed. Boston College was coming off its best season in school history, finishing 26-4 and winning the Big East, led by the conference's Player of the Year, Troy Bell. But Southern Utah had their own Conference Player of the Year in Jeff Monaco, and the senior point guard had a game-high 26 points, including six three-pointers made. The difference in the game was rebounding, where the Eagles used their size advantage to nab 30 offensive boards. After Southern Utah took a six point halftime lead, Bell scored 16 of his 18 points in the second half to lead Boston College back. Bell also had the game-clinching rebound, grabbing it with 13 seconds left off a miss by Southern Utah's Xavier Singletary with the Eagles clinging to a 66-65 lead. After Bell hit the two ensuing free throws, the final three-point attempt from Southern Utah's Justin Sant was short and Boston College escaped. The Thunderbirds are now members of the Big Sky Conference, and have had just one winning season since '00-'01, a 16-14 campaign in '06-'07.
20) #12 Butler vs. #5 Florida, 2000
Though surprise upsets are the essence of March Madness, it's often been favorites just hanging on that has produced many of the tournament's all-time greatest buzzer beaters. From Christian Laettner's iconic turn-around jumper to Tyus Edney's coast-to-coast drive to Mike Miller's runner that saved Florida from Butler in 2000. What made this game even more special is what happened after, as Florida rode the winning momentum all the way to the school's first National Final appearance. After reaching the Final Four in 1994 and then losing coach Lon Kruger, Florida had slowly rebuilt under Billy Donovan and won 24 games in '99-'00 thanks to super sophomores Miller and Udonis Haslem. Butler led for essentially the entire game, with their suffocating defense hampering the Gators' drive-and-dish attack, but blew a seven-point lead late in regulation as Florida forced overtime. With eight seconds left in the extra period and the Bulldogs leading 68-67, star junior guard LaVall Jordan, an 83% free throw shooter, was sent to the line. He missed both, and Florida's Teddy Dupay grabbed the rebound and sent it ahead to Miller, who drove to the basket and hit a hanging leaner to give Florida a 69-68 walk-off win (video here). The emboldened Gators dispatched former coach Kruger's Illinois in the second round, then upset Duke and Oklahoma State to reach the Final Four, where they eventually lost to Michigan State in the title game.
21) #12 Princeton vs. #5 California, 1997
22) #13 Princeton vs. #4 Kentucky, 2011
23) #12 Princeton vs. #5 Notre Dame, 2017
After becoming the Patron Saints of the First Round Near Upset with their 1989 loss to Georgetown, Princeton finally finished the job in 1996, stunning the defending national champions UCLA as a #12 seed. Always a favorite of journalists and basketball nerds for their no-nonsense coach, Pete Carril, "Princeton style" offense of backdoor cuts, and endless parade of clean-cut egghead athletes, the Tigers became an even more populist Cinderella pick heading into 1997. They faced another Pac-10 opponent in Cal, who looked exceedingly vulnerable after losing their star player, Ed Gray, with a broken foot in late February. Princeton was dealing with some personnel adversity of its own, with longtime assistant Bill Carmody having replaced the legendary Carril after his retirement. Employing their signature stingy, patient style, Princeton led 29-23 at halftime, but the Bears roared back in the second frame behind Tony Gonzalez. The two-sport star was just a month away from being drafted by the Kansas City Chiefs, but on this night saved Cal on the hardwood. He scored the team's final five points, including a clutch jumper that gave the Bears a 52-50 lead with 58 seconds left, then two free throws with 14 seconds left to maintain a 55-52 advantage. Gabe Lewullis, who hit the game winner against UCLA a year prior, had a good look at a three-pointer to tie at the buzzer, but it was partially blocked and Cal escaped. 14 years later the Tigers were a chic upset pick again as a #13 seed, taking on an impossibly talented but inexperienced opponent in Kentucky. The Wildcats were ultimately on their way to the Final Four, and though they'd later defeat Ohio State and North Carolina, it was Princeton who staged their biggest challenge along the way. With the scored tied 57-57, Kentucky freshman Brandon Knight, who had missed his last seven field goal attempts, ran down the clock and drove to the hoop, sinking a finger-roll with two seconds remaining. Princeton had one last chance, but had to go the length of the court, and a final half-court heave was well off the mark. Six years later, the Tigers returned to the tournament and were back at it again, this time giving Notre Dame all they could handle. The Fighting Irish held an 11-point second half lead but nearly squandered it down the stretch. Princeton's Devin Cannady had a chance to win it, but missed a three-pointer with seven seconds left as Notre Dame held on, 60-58.
24) #15 Belmont vs. #2 Duke, 2008
Despite understanding the carnage it would unleash on our bracket predictions, most of us can't help but still pull for the underdog. And if they're playing against Duke, all the better. When the Blue Devils lost to VCU in 2007, it was the first opening round upset in Coach K's tenure, which at that point had lasted 26 years and featured 10 Final Fours and three national championships. This stood in stark contrast to Belmont, their first round opponent in 2008, who had never won an NCAA Tournament game and were making just their third appearance. But not only did the Bruins hang with Duke, they held a 70-69 lead with just two minutes remaining. Appearing rattled by their inability to put the game away (despite leads as large as 10 points in the second half) and the raucous D.C. crowd rallying against them, Duke were able to tighten up on defense down the stretch, preventing Belmont from scoring a single point in those final two minutes. Though the Blue Devils struggled to score themselves, they did get a driving lay-up from Gerald Henderson with 11.9 seconds left to take a 71-70 lead. Belmont had two subsequent chances to win it, their first ending on a turnover, and the second when a long three-pointer from Justin Hare just missed. Four years later, the ultimate in NCAA Tournament schadenfreude finally did ensue, when the Blue Devils were stunningly eliminated as a #2 seed in the first round at the hands of Lehigh. Belmont is still winless in the NCAA Tournament in seven total tries.
25) #14 St. Bonaventure vs. #3 Florida State, 2012
The second day of the 2012 NCAA Tournament was a historic one. For the first time in tournament history, two #15 seeds pulled first round upsets, Lehigh over Duke and Norfolk State over Missouri, and even more dubiously did it on the same day. #13 seed Ohio also upset Michigan, making it the first single day in an NCAA Tournament with three teams seeded #13 or lower winning. There was quite nearly a fourth. St. Bonaventure was a huge surprise even making it to the big dance in the first place, claiming the Atlantic-10 automatic bid as the conference's #4 seed, spurred on by their star power forward, Andrew Nicholson. It was the Bonnies' first tournament appearance since they almost stunned Kentucky in 2000 (see #11 above) and they were taking on a Florida State team fresh off an ACC title and marked by many as a dark horse Final Four threat. But St. Bonaventure dominated the first half, and still led 43-35 early in the second half. Florida State then took over, going on a 16-2 run to take an eight-point lead, but St. Bonaventure refused to go away. There were several late chances for the Bonnies to tie the game, but Da'Quan Cook's final two attempts were awry. Possibly rattled by the experience, Florida State would be upset two days later by Cincinnati.
26) #14 George Mason vs. #3 Maryland, 2001
Just a few years before their stunning journey to the Final Four, George Mason almost put themselves on the college basketball map with a win over an eventual Final Four team. Jim Larranaga made an immediate impact with the Patriots, taking the squad to the NCAA Tournament in 1999, his second year as coach. The '00-'01 team was the first to feature only his recruits, and it boasted three senior starters (plus the coach's son, Jon) that upset UNC-Wilmington for the CAA title. One of those seniors, George Evans, scored a game-high 27 points against Maryland, but also committed a turnover with six seconds left that essentially sealed George Mason's fate. Evans was a man playing amongst boys, a 30-year-old Army vet who was reigning CAA Player of the Year for three consecutive seasons, and he kept the Patriots in the game the whole way. Juan Dixon had 22 points for the Terrapins, and after a pass went through Evans' legs out of bounds with six seconds left, Dixon nailed a pair of free throws for an 83-80 lead. Tremaine Price put up a desperation heave at the buzzer to tie it, but it was well off the mark. Maryland defeated former coach Lefty Driesell's Georgia State in the second round, then knocked off Georgetown and Stanford to reach the Final Four. Five years later, the Patriots wreaked havoc on the bracket, defeating Michigan State, North Carolina, Wichita State, and Connecticut on their own trip to the Final Four.
27) #13 Valparaiso vs. #4 Maryland, 2015
14 years after they escaped against George Mason en route to the Final Four, Maryland was back in the tournament for the first time under coach Mark Turgeon. After taking over from Gary Williams in 2011, Turgeon had rebuilt the Terrapins into a Final Four contender in their first season in the Big 10. Their initial tournament opponent was a program that had pulled off one of the most famous first round upsets in March Madness history. Led by coach Homer Drew, Valparaiso made a magical run through the 1998 tournament, starting with a thrilling buzzer beater to cap a first round victory over Mississippi. That shot was hit by Homer's son Bryce, who was the team's star and after a brief NBA career had returned to Valparaiso to take over the coaching position from his father. With power forward Alec Peters leading the way with 18 points, the Crusaders hung tough throughout the game even as they trailed for most of it. Possessing the ball and trailing 65-62 with 14 seconds left, Valparaiso had a chance for Drew to draw up a new miraculous play that could live on forever in school lore. But the Crusaders couldn't even get a shot off as Maryland's Varun Ram, a walk-on that played only in the final 14 seconds of the game, stole the ball in the final seconds to ice the game.
28) #13 New Mexico State vs. #4 San Diego State, 2014
Since reaching the second round in 1993 as a #7 seed, New Mexico State has lost 10 straight NCAA Tournament games, but they came close enough in 2014 to force overtime. The Aggies had cruised to the WAC title that year, thanks in large part to sophomore Sim Bhullar. Born in Canada to Indian parents, the 7'5", 350 pound Bhullar would brutalize college opponents in the paint. This game was no different, as the undersized front line for San Diego State struggled to contain Bhullar, who finished the game with 14 points and seven rebounds. But the Aztecs, led by star guard Xavier Thames with 23 points, jumped out to a sizable lead before the Aggies slowly eroded it in the second half, outscoring San Diego State 14-4 in the final three minutes to tie the game at 60-60 and send it to overtime. After Bhullar fouled out early in the extra frame, San Diego State eventually held on for a 73-69 win. After declaring early for the draft that summer, Bhullar would eventually sign with the Sacramento Kings and become the first player of Indian descent to play in the NBA.
29) #16 Fairleigh Dickinson vs. #1 Michigan, 1985
30) #16 Murray State vs. #1 Michigan State, 1990
31) #16 Western Carolina vs. #1 Purdue, 1996
Though Princeton in 1989 was the most famous example, and UMBC in 2018 was the first actual upset, it's worth remembering the other moments when a #16 seed came achingly close to upsetting a top seed in the first round. That all three of these near misses came against a Big 10 team may or may not be a coincidence. The first was in 1985, when the NCAA first expanded to a 64-team tournament, which Fairleigh Dickinson qualified for by winning the now defunct mouthful known as the Eastern Collegiate Athletic Metro Conference. There was already a palpable buzz in Dayton on the day they matched up against Michigan, as David Robinson and Navy had already upset LSU earlier in the day, while Maryland needed overtime to hold off Miami (OH) (see #10 above). Playing a slowed-down half court style to frustrate the Wolverines, Fairleigh Dickinson held a 32-22 lead with 15 minutes left, but couldn't hang on down the stretch, with star Roy Tarpley ultimately hitting a pair of free throws to seal the game for Michigan with a final score of 59-55. Two days later, the Wolverines would be upset by Villanova, who eventually became the only #8 seed to win a national championship.
Their cross-state rivals, Michigan State, soon became the first, and still only, top seed to be taken to overtime by a #16 seed. Led by Steve Smith, the Spartans were enjoying their best season in school history in '89-'90 while Murray State, starring Popeye Jones, had come seemingly out of nowhere to capture the Ohio Valley Conference title. Jones dominated their first round matchup, scoring 37 points, but it was his teammate Greg Coble who provided the dramatics, hitting a buzzer beating three-pointer to send the game to overtime tied at 65-65. It was Frank Allen's turn in overtime for Murray State, hitting a clutch three-pointer to tie the game at 71-71, but then Michigan State's Kirk Mann hit a beautiful reverse lay-up to give the Spartans the lead for good, as they held on 75-71. Michigan State survived another tough upset bid from UC Santa Barbara in the second round before losing in overtime to Georgia Tech in the Regional Semifinals.
As for Purdue, a few heads were turned when the Boilermakers were handed a top seed in the 1996 NCAA Tournament. No doubt the team had enjoyed a fine season, but they were seen as a paper tiger in a down year for the Big 10. Though few expected them to be a realistic championship threat, no one dared to believe they may actually be toppled in the first round. Western Carolina were playing in their first tournament, having shocked Davidson to win the Southern Conference crown. After Purdue's Brad Miller missed the front end of a one-and-one with 11.6 seconds left and a 73-71 lead, the Catamounts found themselves in the position of going for a win or tie. The ball made its way to point guard Joel Fleming, whose 3-pointer looked true, but just rolled off the rim. Joe Stafford grabbed the rebound for Western Carolina and put up an off-balance runner at the buzzer to try to force overtime, but it also bounced off the rim and Purdue survived to advance. The game turned out to be more of an omen than a blip for the Boilermakers, who were upset by Georgia in the second round. Western Carolina has not returned to the tournament since, but their close call will live on forever, even after UMBC finally followed through on the impossible in 2018. As then Western Carolina coach Phil Hopkins stated after the game, in a reverse paraphrasing of John Thompson from 1989, "we didn't just deserve to keep it close, I thought we deserved to win."
When Maryland-Baltimore County finally became the first 16 seed to upset a top seed (Virginia) in the 2018 NCAA Tournament, all college basketball junkies knew the clip that was going to be played to commemorate the event. Princeton alumni and fans probably know it by heart. Kirk Mueller, a sophomore center, his lip still swollen from getting an elbow from his Georgetown counterpart, Alonzo Mourning, earlier in the game, putting up a final potential game-winning shot at the buzzer, blocked (some would say while being fouled) by Mourning. "The Hoyas escape, and I mean escape" was the final call from Billy Packer, and for good reason. Coming into the tournament that year there had been talk of eliminating the automatic bid for small conferences, but this game may have single-handedly saved it for the next 30 years and counting. It received a large amount of pregame hype for what many considered to be a sure blow-out, including a young ESPN analyst named Dick Vitale who promised to don a cheerleader outfit and serve as a ball boy for Princeton in their second round game if they pulled off the upset (unless you're a Georgetown fan, missing out on that visual was probably the only upside to Princeton not pulling off the upset). Utilizing coach Pete Carrill's "Princeton" offense and possessing the nation's best defense, the Tigers took a shocking 29-21 lead at halftime. Even in the era before cell phones and Twitter, word spread fast and TV sets around the country tuned in en masse for the second frame. Georgetown stormed back, and took the lead 50-49 when Mourning hit one of two free throw attempts with 18 seconds remaining. Mourning then blocked not one, but two potential game winners in the waning moments, knocking one out of bounds at the six second mark which set up Mueller's final attempt (you can watch the entire sequence here). After the game, Georgetown coach John Thompson remarked "it's an understatement to say that Princeton deserved to win." Agreed. But in the process, they inspired countless generations of little guys with slingshots, up to and including the UMBC Retrievers.
2) #16 East Tennessee State vs. #1 Oklahoma, 1989
The Princeton-Georgetown game so dominated the narrative of the 1989 NCAA Tournament, both at the time and in retrospect, that most have forgotten that another #16 seed almost pulled off the improbable that same weekend. From the time the NCAA expanded to 64 teams in 1985 to UMBC upsetting Virginia in 2018, a #16 seed came within a basket of winning just four times, and two of those came in 1989. Perhaps most amazing for East Tennessee State is that unlike Princeton, they actually led by a wide margin for much of the game, including by as much as 17 points in the first half. The Sooners, defending National runners-up and led by star point guard Mookie Blaylock, methodically chipped away at the lead in the second half, as East Tenneessee State went ice cold from the field. When Blaylock hit a driving lay-up to give Oklahoma a 72-71 lead with 1:21 left, it was only their second lead of the game and it turned out to be the final score, as both squads struggled to connect down the stretch, and a final half-court heave from Alvin West couldn't find net (someone put the entire game on YouTube, if you're inclined to watch). Oklahoma was eventually upset in the Regional Semifinals by #5 seed Virginia, while the Buccaneers made their mark three years later as a #14 seed, upsetting Arizona in the first round of the 1992 tournament. In addition to Georgetown and Oklahoma, top seeded Illinois also struggled on that fateful Thursday in March, holding on for a six-point victory over #16 seed McNeese State.
3) #15 Georgia Southern vs. #2 Syracuse, 1987
Not much was expected of Syracuse in '86-'87 after their star guard Pearl Washington had left early for the NBA. But sparked by Sherman Douglas and freshman sensation Derrick Coleman, the Orange grinded out a surprise 31-7 record and a #2 seed in the NCAA Tournament. As luck would have it, their home base, the Carrier Dome, was hosting tournament games that season, and few foresaw the Orange struggling in the first two rounds in literal home games. Their first opponent, Georgia Southern, were unexpected champions of the Atlantic Sun conference and playing in just their second NCAA Tournament game in school history. But the Eagles from tiny Statesboro, GA would not go quietly, leading 40-39 at halftime and continually coming from behind in the second half when the Orange tried to put the game away. Senior guard Greg Monroe (no relation to the future Georgetown and Pistons star) was finally able to seal it with a series of clutch three-pointers and Syracuse moved on, 79-73. Locked in after the near-upset, the Orange made it all the way to their first National Final appearance, losing to Indiana on Keith Smart's dramatic game winner. Georgia Southern has returned to the tournament just once since, a blowout first round loss as a #15 seed in 1992.
4) #12 UW-Milwaukee vs. #5 Notre Dame, 2003
The 12-over-5 upset has become so prevalent annually in the NCAA Tournament that even the most novice of bracket prognosticators knows to pick at least one in their office pool entry. Occasionally that can work against you, when a highly-touted #12 seed comes up just short, as was the case with Wisconsin-Milwaukee in 2003. Coached by Bruce Pearl, the Panthers were making their first tournament appearance in school history, but many had them pegged as a prime upset opportunity against a vulnerable-looking squad from Notre Dame. Things looked especially dire for the Irish when their star forward Matt Carroll left late in the first half with an apparent sprained ankle. But they still had point guard Chris Thomas, who led all scorers with 27 points, and freshman power forward Torin Francis, who hit the eventual game winner on a put-back with 32 seconds left. Trailing by one, Milwaukee's best player, Clay Tucker (who has enjoyed a long pro career in Europe), had the ball in his hands at the end, but when he was triple-teamed driving to the hoop he dished to open teammate Dylan Page, who couldn't put in a jump hook at the buzzer. Carroll returned from his injury in the second round for Notre Dame, who managed to reach the Sweet 16. Milwaukee returned to the tournament as a #12 seed in 2005 and on the second try pulled off the vaunted upset over Alabama.
5) #14 Pepperdine vs. #3 Michigan, 1994
Though Michigan's Fab Five officially ceased to be following the 1993 NCAA Championship Game, when Chris Webber declared early for the NBA draft, the Wolverines were still a dangerous team in '93-'94. The roster featured the other four members of the highly touted 1991 recruiting class: Juwan Howard, Jalen Rose, Jimmy King, and Ray Jackson, now all juniors. Entering the NCAA Tournament as a #3 seed, they were determined to prove themselves a viable Final Four threat even without Webber, and were eventually were able to do so, but not until surviving a scare from Pepperdine. A mid-sized, scenic, private school located in the hills of Malibu, the Waves had become a perennial tournament fixture in the '80s and early '90s under coaches Jim Harrick and Tom Asbury, but were looking for their first postseason victory in 12 years. When the two teams locked up in Wichita, Michigan led for much of the way but the game, and the crowd, turned against the Wolverines when Howard committed a hard foul with a subsequent stare-down of Damin Lopez, Pepperdine's diminutive point guard. Seemingly inspired by the taunt, Lopez heated up down the stretch, hitting five three-pointers in the second half. He had a chance to win the game in regulation, but his last second shot was blocked by Rose. Michigan played strong in overtime, hitting all ten of their free throws to pull away for a 78-74 win. After further close wins over Texas and Maryland, Michigan lost in the Regional Finals against the eventual national champs from Arkansas. Pepperdine finally won a tournament game in 2000, upsetting Bob Knight's Indiana as a #11 seed.
6) #15 Robert Morris vs. #2 Villanova, 2010
The tournament had been nine years removed from a 15 seed upsetting a 2 seed when Robert Morris took the floor against Villanova on the opening Thursday of its 2010 edition. The Wildcats were obviously heavily favored, having reached the 2009 Final Four, but their confidence was slightly tempered before tip-off when it was announced that back court starters Scottie Reynolds and Corey Fisher were being benched for an apparent off-court infraction. Though coach Jay Wright called it a "teaching point," neither benching lasted long, but Reynolds struggled to find his rhythm, possibly as a result. With just over four minutes to play in the game, the star shooting guard was just 2-of-15 from the floor, and Robert Morris held a 55-47 lead. Galvanized by the performance of their own star guard, Karon Abraham, the Colonials seemed primed to join Hampton, Coppin State, Richmond, and Santa Clara in the hallowed annals of #15 seed victors. But then Reynolds did something all great players should do when struggling to shoot: he got himself to the free throw line, hitting 15-of-16 from the charity stripe to help lead the Wildcats back and send the game to overtime. Villanova then hung on for dear life in the extra period, ultimately winning the game 73-70 when Robert Morris' Meize Nwigwe was errant on a desperation three-pointer. It probably wasn't the lesson Wright intended to "teach" Reynolds, but it all worked out, at least for one night. Two days later Villanova was ousted by #10 seed Saint Mary's.
7) #13 La Salle vs. #4 Seton Hall, 1992
Seton Hall had a perfectly fine season in '91-'92, though it didn't quite live up to expectations. Returning their best player, Terry Dehere, from a team that won the Big East and reached the Elite Eight in 1991, they were upset in the semifinals of the 1992 Big East Tournament and entered the NCAA Tournament as a #4 seed. Their first round opponent was La Salle, soon to be an Atlantic-10 member, but then the champions in their final season in the MAAC. The Explorers were no stranger to March pressure, playing in their fourth tournament in five years under coach Speedy Morris. Their star player Randy Woods averaged 27.3 points per game and didn't disappoint against the Pirates, netting 21 points in the first half and staking La Salle to an early lead. Trailing by eight with just 4:12 left on the clock, Seton Hall was finally able to muster a comeback thanks to John Leahy, who scored nine straight points himself down the stretch, and set up the game-winning shot by Dehere. Like many Cinderella hopefuls, La Salle lived and died by the three-pointer, and struggled down the stretch to finish just 9-of-30 for the game. The Explorers would not return to the NCAA Tournament again until 2013, when this time as a #13 seed they pulled off two upsets and reached the Sweet 16.
8) #15 Texas Southern vs. #2 Arkansas, 1995
Coming into the 1995 tournament, Texas Southern was no stranger to being a #15 seed taking on a traditional power in the first round. The year prior they had taken on Grant Hill and Duke, putting up a fight but losing 82-70. Duke went on to reach the National Final and lose to Arkansas, who was Texas Southern's first round opponent in 1995, and also a team they were already familiar with. That wasn't necessarily a good thing in this case, as the Razorbacks had defeated the Tigers during the '93-'94 regular season by 66 points. The story line was different this time, even after Arkansas opened an early 17-point lead. Texas Southern fought back to take a lead early in the second half, then fell behind again by 10 before mounting a final comeback. After Corliss Williamson gave the Razorbacks a 79-76 lead with 27 seconds left, Texas Southern's Randy Bolden had to chance to essentially live out a childhood driveway hoop dream. He was fouled while shooting a three-pointer with 6.1 seconds left, and was granted a trio of free throws to tie the game. The team's best free throw shooter, at 80%, Bolden hit the first two, but was short on the third, allowing Arkansas to escape. The immediacy of the close call wasn't lost on their coach, Nolan Richardson, who chided his team after the game for their poor play. That coaching strategy seemed to work, as Arkansas won their next two games in overtime and eventually made it all the way back to the National Final, this time losing to UCLA. Texas Southern has made five more tournament appearances since 1995, but is still searching for their first postseason win.
9) #13 Pacific vs. #4 Boston College, 2006
Nobody wanted to draw Pacific in the 2006 NCAA Tournament. After upsetting Providence as a #12 seed in 2004 they followed it up with a first round win over Pittsburgh in 2005, and the senior-laden Tigers had cruised to a third straight Big West title to enter 2006 as a #13 seed. Boston College, considered a dark horse Final Four contender with their star upperclassmen Craig Smith and Jared Dudley, drew the unlucky straw. The game was played in Salt Lake City, closer to Pacific's home in Northern California, and the crowd was decidedly backing the underdog Tigers anyway. Pacific's star power forward Christian Maraker did not disappoint, finishing with 30 points and 9 rebounds, and hitting a clutch three-pointer that capped a 13-point comeback and sent the game to overtime. The extra period was back-and-forth, with a pair of free throws from Smith (who finished with 25 points and 13 rebounds) tying the game at the end of the first overtime after a controversial foul call against Maraker. Boston College proceeded to score the first nine points of second overtime and pulled away for an 88-76 win. The Eagles did reach the Sweet 16, where they lost to top seeded Villanova in overtime.
10) #12 Miami (OH) vs. #5 Maryland, 1985
After his untimely death that occurred before he ever played an NBA game, Len Bias has become something of a spectral presence whose NCAA career has only grown exponentially in awed stature, with tapes of his games at Maryland passed around like Grateful Dead bootlegs. Though the majority of Bias' greatest moments came in the regular season and ACC Tournament rather than the NCAA Tournament, one exception came in the first round in 1985, when the Terps were being tested by Miami (OH). The Redhawks had a superstar of their own, Ohio-bred Ron Harper, and he pushed Bias to the brink in this match-up. Harper finished the game with 26 points, Bias with 25, and both shot exceptionally well from the field throughout as they dueled. After coming back from an 11-point second half deficit, Miami sent the game to overtime at 59-59. They seemed primed to put the game away late in the extra period, when Harper threw down a posterizing dunk that not only gave Miami a three-point lead, but also put him at the line while fouling out Bias (just watch this highlight, if you're ever questioning just how good Harper was before injuries set in). Harper missed the free throw, and Maryland's Adrian Branch hit a jumper to cut the lead to one, then stole the ensuing inbounds pass and passed the ball to Jeff Adkins, who laid in the game winner. Maryland needed another comeback and another huge game from Bias to avoid an upset at the hands of Navy in the second round, and then eventually fell to #8 seed and eventual national champions Villanova in the Regional Semifinals. Harper and Miami returned to the 1986 tournament as a #10 seed, but fell just short again in another first round upset bid against Iowa State.
11) #12 St. Bonaventure vs. #5 Kentucky, 2000
When Kentucky lost in the first round of the NCAA Tournament to Marquette in 2008, it was their first such loss in 21 years. The closest they had come during that stretch to dropping a game so early in the big dance was this instance in 2000, when they were one year removed from winning the national championship. The Wildcats slumped in '99-'00, despite the presence of Jamaal Magloire and Tayshaun Prince, and came into the tournament looking like a prime upset victim as a #5 seed. Their first round opponent was St. Bonaventure, who was making their first tournament appearance in 22 years but was a solid defensive team with several upperclassmen, making them a dangerous early opponent. After falling behind by 13 points early in the second half, the Bonnies went on a 21-4 run to take the lead, with a Prince three-pointer eventually sending the game to overtime (St. Bonaventure guard Tim Winn had a chance to win it in regulation, but his coast-to-coast lay-up rimmed out at the buzzer). Already shorthanded due to a suspension of Desmond Allison for a DUI, Kentucky lost their starting point guard Saul Smith (coach Tubby's son) and backup center Jules Camara to injuries during the game, but still led for most of both overtimes. They had the game in hand late in the first extra period, but an inexplicable foul of St. Bonaventure guard David Capers allowed him to nail three free throws with 0.4 seconds left to send the game into a second overtime. The second overtime was close, but a missed three-pointer by Winn with three seconds left that could have tied the game allowed the Wildcats to ice the contest at the free throw line, 75-70. 12 years and three coaches later, St. Bonaventure finally returned to the tournament, but lost another close upset bid (see entry #25 below).
12) #15 Utah State vs. #2 Kansas, 2003
After finishing the season 25-7 and winning a difficult Big 12, Kansas assumed it deserved a #1 seed in a wide-open 2003 NCAA Tournament field. Feeling insulted by the #2 seed they received, the Jayhawks travelled to nearby Oklahoma City for what they expected to be a virtual tune-up against Utah State, but instead found themselves in a fire fight. Though Kansas never trailed in the game, they never built a comfortable lead either, often extending the lead to seven or eight points only for the Aggies to continually bring it back to one or two. Utah State senior forward Desmond Penigar led all players in scoring and rebounding, including what was ultimately the last basket of the game, a three-pointer that cut the lead to 64-61 with 47 seconds left. Penigar also had a chance to tie it after a Kansas turnover, but missed a three-pointer with just a few seconds remaining. Led by Nick Collison and Kirk Hinrich, Kansas cruised along past Arizona State, Duke, and Arizona en route to the Final Four, before losing to Carmelo Anthony and Syracuse in the Championship Game.
13) #15 Northern Arizona vs. #2 Cincinnati, 1998
Led by Ruben Patterson and Kenyon Martin, Cincinnati came into the 1998 tournament primed to atone from losing in a second round upset as a #3 seed the year prior. A postseason underachiever pall was starting to hang over Bob Huggins' program, and a first round match-up against a feisty Northern Arizona team playing closer to home in Boise looked like a dangerous proposition. The underdog Lumberjacks led the entire game until about the 16 minute mark of the second half, when the Bearcats took over the lead and held on the rest of the way. Cincinnati wisely avoided the trap that many high seeds fall into against smaller conference schools, and made full utilization of their size advantage. They pounded the ball inside, decimating the smaller Northern Arizona front line, getting them into early foul trouble and dominating the rebounding totals 41-26 (Martin grabbed 15 of them). D'Juan Baker hit the game winner for Cincinnati, a three-pointer with 3.6 seconds left to take a 65-62 lead, and Kawika Akina's desperation potentially tying heave for Northern Arizona clanged harmlessly off the rim. The Bearcats were upset in the next round anyway by West Virginia, and would return to the Sweet 16 just one more time under Huggins, in 2001. Northern Arizona has returned to the tournament just once time since this game, again as a #15 seed in 2000, and again putting a scare into their heavily favored opponent, St. John's.
14) #12 Iona vs. #5 Syracuse, 1998
It became a moot point when they won the 2003 championship, but for a long time Jim Boeheim's Syracuse teams had a reputation as an NCAA Tournament underachiever, despite Final Four appearances in 1987 and 1996. They suffered a historic first round upset against Richmond as a #2 seed in 1991, and had been additionally ousted by a lower seed in 1984, 1988, and 1990. After missing the tournament altogether in 1997, Syracuse entered the 1998 edition in the traditional land mine position of a #5 seed taking on a #12 seed. Even more intriguing was their opponent Iona being coached by former Boeheim assistant Tim Welsh, who had built a classic upset-minded roster, populated with a heavy dose of upperclassmen and outside shooters that had secured early season wins against Big East opponents Rutgers and Providence. The game was back-and-forth in the second half, with 10 lead changes over the final 10 minutes. The ninth lead change was Iona's John McDonald hitting a three-pointer with 24 seconds left to give his team a 61-60 advantage. On the ensuing possession, Syracuse's Todd Burgan took the ball inside, had his initial attempt blocked, recovered, and dished outside to a wide-open unlikely hero, Lithuanian Marius Janulis, who drained a three-pointer with 1.2 seconds on the clock. After Iona were unable to properly inbound to get off a final shot, the Orange breathed a heavy sigh of relief and moved on, eventually reaching the Sweet 16.
15) #15 East Tennessee State vs. #2 Wake Forest, 2003
16) #13 East Tennessee State vs. #4 Cincinnati, 2004
Under coaches Les Robinson and Alan LeForce, East Tennessee State was one of the nation's top mid-major programs in the late '80s and early '90s, producing some great tournament moments including a stunning upset of Arizona as a #14 seed in 1992. The program fell apart for a while, but returned to prominence under Ed DeChellis in '02-'03, winning the Southern Conference to secure a tournament bid as a #15 seed. Their first round opponent was Wake Forest, who was led by Josh Howard and enjoying their best season since Tim Duncan left for the NBA. Howard struggled offensively in this game, scoring just 12 points, but added some crucial shutdown defense and hit two clutch free throws that broke a 72-72 tie with 21 seconds left. Dynamic freshman point guard Tim Smith, who led all scorers in the game with 22, had a chance to tie the game for East Tennessee State at the buzzer, but missed a baseline three-pointer and Wake Forest escaped, 76-73. Smith was one of four starters that returned for East Tennessee State in '03-'04, and they were pegged as a leading Cinderella candidate heading into that tournament as a #13 seed. Trailing in their first round game late against Cincinnati, Smith, who was the game's leading scorer with 26, had a chance to cut Cincinnati's lead to one with 16 seconds left, but missed a driving lay-up and the Bearcats were able to run out the clock for an 80-77 win. Though Smith spent two more years at the school, and eventually won the conference Player of the Year award, he was unable to guide the Buccaneers back to the tournament.
17) #13 UC-Irvine vs. #4 Louisville, 2015
After waiting 40 years for their first NCAA Tournament appearance, the Anteaters of UC-Irvine made it count. Showing no signs of being rattled by matching up against a Rick Pitino-coached Louisville team just two years removed from being national champions, UC-Irvine leaned on their Senegalese sensation Mamdou N'Diaye, who was the tournament's tallest player at 7'6". Able to finish with dunks at the rim without even leaving his feet and swat away shot attempts with ease, N'Diaye electrified the Seattle crowd and finished the game with 12 points and five rebounds. It was a back-and-forth affair, with neither team ever leading by more than seven points, and with 43 seconds left Louisville's Wayne Blackshear made a courageous lay-up by going right at N'Diaye to tie the game at 55-55. After the Anteaters' Luke Nelson missed a three-pointer on the ensuing possession, the Cardinals iced it with a pair of free throws by Quentin Snider, then a steal in the closing seconds. Louisville eventually reached the Regional Finals before losing to Michigan State. Despite N'Diaye returning for his junior year, UC-Irvine failed to make the NCAA Tournament in 2016 after they were upset in the Big West Tournament semifinals.
18) #15 Winthrop vs. #2 Tennessee, 2006
Outside of Kentucky and Florida, the SEC has struggled immensely through the years in the NCAA Tournament, with its top teams often vulnerable to early upsets. Tennessee has been far from immune from that syndrome, and in 2006, when they were making their first return to the tournament in five years, many saw the Vols as over seeded and susceptible. They were done no favors by the selection committee, who matched up Tennessee against Winthrop, a well-coached (by Gregg Marshall, now the coach at Wichita State) and battle-tested team that was located close to the game site of Greensboro, NC. With multiple ties and lead changes, the game was a thrilling one until both offenses stalled late with the score tied 61-61. After multiple turnovers and difficult shots, Winthrop finally got a good look from Craig Bradshaw with 38 seconds left, but his three-pointer was errant, setting up Tennessee's final play. First year coach Bruce Pearl (who knew a thing or two about near-upsets from the other side, see #4 above) drew up the inbounds play for C.J. Watson, but it ended up in the hands of Chris Lofton, who drilled a three-pointer with 0.4 seconds left to finish the game (you can watch it here). Lofton's teammates mobbed him in celebration, and it would be Tennessee's only jubilation that March, as they were upset by #7 seed Wichita State in the next round. Winthrop returned to the tournament in 2007 as a #11 seed, and after seven previous unsuccessful attempts, finally won the first tournament game in school history, an upset over Notre Dame.
19) #14 Southern Utah vs. #3 Boston College, 2001
Southern Utah has been a Division I team for 30 years and counting but have made just one NCAA Tournament appearance in that time. And though they may have lost that one game, they sure did make it interesting. Surprise champions in 2001 of the now-defunct Mid-Continent Conference, the Thunderbirds were hardly a chic upset pick heading into the big dance as a #14 seed. Boston College was coming off its best season in school history, finishing 26-4 and winning the Big East, led by the conference's Player of the Year, Troy Bell. But Southern Utah had their own Conference Player of the Year in Jeff Monaco, and the senior point guard had a game-high 26 points, including six three-pointers made. The difference in the game was rebounding, where the Eagles used their size advantage to nab 30 offensive boards. After Southern Utah took a six point halftime lead, Bell scored 16 of his 18 points in the second half to lead Boston College back. Bell also had the game-clinching rebound, grabbing it with 13 seconds left off a miss by Southern Utah's Xavier Singletary with the Eagles clinging to a 66-65 lead. After Bell hit the two ensuing free throws, the final three-point attempt from Southern Utah's Justin Sant was short and Boston College escaped. The Thunderbirds are now members of the Big Sky Conference, and have had just one winning season since '00-'01, a 16-14 campaign in '06-'07.
20) #12 Butler vs. #5 Florida, 2000
Though surprise upsets are the essence of March Madness, it's often been favorites just hanging on that has produced many of the tournament's all-time greatest buzzer beaters. From Christian Laettner's iconic turn-around jumper to Tyus Edney's coast-to-coast drive to Mike Miller's runner that saved Florida from Butler in 2000. What made this game even more special is what happened after, as Florida rode the winning momentum all the way to the school's first National Final appearance. After reaching the Final Four in 1994 and then losing coach Lon Kruger, Florida had slowly rebuilt under Billy Donovan and won 24 games in '99-'00 thanks to super sophomores Miller and Udonis Haslem. Butler led for essentially the entire game, with their suffocating defense hampering the Gators' drive-and-dish attack, but blew a seven-point lead late in regulation as Florida forced overtime. With eight seconds left in the extra period and the Bulldogs leading 68-67, star junior guard LaVall Jordan, an 83% free throw shooter, was sent to the line. He missed both, and Florida's Teddy Dupay grabbed the rebound and sent it ahead to Miller, who drove to the basket and hit a hanging leaner to give Florida a 69-68 walk-off win (video here). The emboldened Gators dispatched former coach Kruger's Illinois in the second round, then upset Duke and Oklahoma State to reach the Final Four, where they eventually lost to Michigan State in the title game.
21) #12 Princeton vs. #5 California, 1997
22) #13 Princeton vs. #4 Kentucky, 2011
23) #12 Princeton vs. #5 Notre Dame, 2017
After becoming the Patron Saints of the First Round Near Upset with their 1989 loss to Georgetown, Princeton finally finished the job in 1996, stunning the defending national champions UCLA as a #12 seed. Always a favorite of journalists and basketball nerds for their no-nonsense coach, Pete Carril, "Princeton style" offense of backdoor cuts, and endless parade of clean-cut egghead athletes, the Tigers became an even more populist Cinderella pick heading into 1997. They faced another Pac-10 opponent in Cal, who looked exceedingly vulnerable after losing their star player, Ed Gray, with a broken foot in late February. Princeton was dealing with some personnel adversity of its own, with longtime assistant Bill Carmody having replaced the legendary Carril after his retirement. Employing their signature stingy, patient style, Princeton led 29-23 at halftime, but the Bears roared back in the second frame behind Tony Gonzalez. The two-sport star was just a month away from being drafted by the Kansas City Chiefs, but on this night saved Cal on the hardwood. He scored the team's final five points, including a clutch jumper that gave the Bears a 52-50 lead with 58 seconds left, then two free throws with 14 seconds left to maintain a 55-52 advantage. Gabe Lewullis, who hit the game winner against UCLA a year prior, had a good look at a three-pointer to tie at the buzzer, but it was partially blocked and Cal escaped. 14 years later the Tigers were a chic upset pick again as a #13 seed, taking on an impossibly talented but inexperienced opponent in Kentucky. The Wildcats were ultimately on their way to the Final Four, and though they'd later defeat Ohio State and North Carolina, it was Princeton who staged their biggest challenge along the way. With the scored tied 57-57, Kentucky freshman Brandon Knight, who had missed his last seven field goal attempts, ran down the clock and drove to the hoop, sinking a finger-roll with two seconds remaining. Princeton had one last chance, but had to go the length of the court, and a final half-court heave was well off the mark. Six years later, the Tigers returned to the tournament and were back at it again, this time giving Notre Dame all they could handle. The Fighting Irish held an 11-point second half lead but nearly squandered it down the stretch. Princeton's Devin Cannady had a chance to win it, but missed a three-pointer with seven seconds left as Notre Dame held on, 60-58.
24) #15 Belmont vs. #2 Duke, 2008
Despite understanding the carnage it would unleash on our bracket predictions, most of us can't help but still pull for the underdog. And if they're playing against Duke, all the better. When the Blue Devils lost to VCU in 2007, it was the first opening round upset in Coach K's tenure, which at that point had lasted 26 years and featured 10 Final Fours and three national championships. This stood in stark contrast to Belmont, their first round opponent in 2008, who had never won an NCAA Tournament game and were making just their third appearance. But not only did the Bruins hang with Duke, they held a 70-69 lead with just two minutes remaining. Appearing rattled by their inability to put the game away (despite leads as large as 10 points in the second half) and the raucous D.C. crowd rallying against them, Duke were able to tighten up on defense down the stretch, preventing Belmont from scoring a single point in those final two minutes. Though the Blue Devils struggled to score themselves, they did get a driving lay-up from Gerald Henderson with 11.9 seconds left to take a 71-70 lead. Belmont had two subsequent chances to win it, their first ending on a turnover, and the second when a long three-pointer from Justin Hare just missed. Four years later, the ultimate in NCAA Tournament schadenfreude finally did ensue, when the Blue Devils were stunningly eliminated as a #2 seed in the first round at the hands of Lehigh. Belmont is still winless in the NCAA Tournament in seven total tries.
25) #14 St. Bonaventure vs. #3 Florida State, 2012
The second day of the 2012 NCAA Tournament was a historic one. For the first time in tournament history, two #15 seeds pulled first round upsets, Lehigh over Duke and Norfolk State over Missouri, and even more dubiously did it on the same day. #13 seed Ohio also upset Michigan, making it the first single day in an NCAA Tournament with three teams seeded #13 or lower winning. There was quite nearly a fourth. St. Bonaventure was a huge surprise even making it to the big dance in the first place, claiming the Atlantic-10 automatic bid as the conference's #4 seed, spurred on by their star power forward, Andrew Nicholson. It was the Bonnies' first tournament appearance since they almost stunned Kentucky in 2000 (see #11 above) and they were taking on a Florida State team fresh off an ACC title and marked by many as a dark horse Final Four threat. But St. Bonaventure dominated the first half, and still led 43-35 early in the second half. Florida State then took over, going on a 16-2 run to take an eight-point lead, but St. Bonaventure refused to go away. There were several late chances for the Bonnies to tie the game, but Da'Quan Cook's final two attempts were awry. Possibly rattled by the experience, Florida State would be upset two days later by Cincinnati.
26) #14 George Mason vs. #3 Maryland, 2001
Just a few years before their stunning journey to the Final Four, George Mason almost put themselves on the college basketball map with a win over an eventual Final Four team. Jim Larranaga made an immediate impact with the Patriots, taking the squad to the NCAA Tournament in 1999, his second year as coach. The '00-'01 team was the first to feature only his recruits, and it boasted three senior starters (plus the coach's son, Jon) that upset UNC-Wilmington for the CAA title. One of those seniors, George Evans, scored a game-high 27 points against Maryland, but also committed a turnover with six seconds left that essentially sealed George Mason's fate. Evans was a man playing amongst boys, a 30-year-old Army vet who was reigning CAA Player of the Year for three consecutive seasons, and he kept the Patriots in the game the whole way. Juan Dixon had 22 points for the Terrapins, and after a pass went through Evans' legs out of bounds with six seconds left, Dixon nailed a pair of free throws for an 83-80 lead. Tremaine Price put up a desperation heave at the buzzer to tie it, but it was well off the mark. Maryland defeated former coach Lefty Driesell's Georgia State in the second round, then knocked off Georgetown and Stanford to reach the Final Four. Five years later, the Patriots wreaked havoc on the bracket, defeating Michigan State, North Carolina, Wichita State, and Connecticut on their own trip to the Final Four.
27) #13 Valparaiso vs. #4 Maryland, 2015
14 years after they escaped against George Mason en route to the Final Four, Maryland was back in the tournament for the first time under coach Mark Turgeon. After taking over from Gary Williams in 2011, Turgeon had rebuilt the Terrapins into a Final Four contender in their first season in the Big 10. Their initial tournament opponent was a program that had pulled off one of the most famous first round upsets in March Madness history. Led by coach Homer Drew, Valparaiso made a magical run through the 1998 tournament, starting with a thrilling buzzer beater to cap a first round victory over Mississippi. That shot was hit by Homer's son Bryce, who was the team's star and after a brief NBA career had returned to Valparaiso to take over the coaching position from his father. With power forward Alec Peters leading the way with 18 points, the Crusaders hung tough throughout the game even as they trailed for most of it. Possessing the ball and trailing 65-62 with 14 seconds left, Valparaiso had a chance for Drew to draw up a new miraculous play that could live on forever in school lore. But the Crusaders couldn't even get a shot off as Maryland's Varun Ram, a walk-on that played only in the final 14 seconds of the game, stole the ball in the final seconds to ice the game.
28) #13 New Mexico State vs. #4 San Diego State, 2014
Since reaching the second round in 1993 as a #7 seed, New Mexico State has lost 10 straight NCAA Tournament games, but they came close enough in 2014 to force overtime. The Aggies had cruised to the WAC title that year, thanks in large part to sophomore Sim Bhullar. Born in Canada to Indian parents, the 7'5", 350 pound Bhullar would brutalize college opponents in the paint. This game was no different, as the undersized front line for San Diego State struggled to contain Bhullar, who finished the game with 14 points and seven rebounds. But the Aztecs, led by star guard Xavier Thames with 23 points, jumped out to a sizable lead before the Aggies slowly eroded it in the second half, outscoring San Diego State 14-4 in the final three minutes to tie the game at 60-60 and send it to overtime. After Bhullar fouled out early in the extra frame, San Diego State eventually held on for a 73-69 win. After declaring early for the draft that summer, Bhullar would eventually sign with the Sacramento Kings and become the first player of Indian descent to play in the NBA.
29) #16 Fairleigh Dickinson vs. #1 Michigan, 1985
30) #16 Murray State vs. #1 Michigan State, 1990
31) #16 Western Carolina vs. #1 Purdue, 1996
Though Princeton in 1989 was the most famous example, and UMBC in 2018 was the first actual upset, it's worth remembering the other moments when a #16 seed came achingly close to upsetting a top seed in the first round. That all three of these near misses came against a Big 10 team may or may not be a coincidence. The first was in 1985, when the NCAA first expanded to a 64-team tournament, which Fairleigh Dickinson qualified for by winning the now defunct mouthful known as the Eastern Collegiate Athletic Metro Conference. There was already a palpable buzz in Dayton on the day they matched up against Michigan, as David Robinson and Navy had already upset LSU earlier in the day, while Maryland needed overtime to hold off Miami (OH) (see #10 above). Playing a slowed-down half court style to frustrate the Wolverines, Fairleigh Dickinson held a 32-22 lead with 15 minutes left, but couldn't hang on down the stretch, with star Roy Tarpley ultimately hitting a pair of free throws to seal the game for Michigan with a final score of 59-55. Two days later, the Wolverines would be upset by Villanova, who eventually became the only #8 seed to win a national championship.
Their cross-state rivals, Michigan State, soon became the first, and still only, top seed to be taken to overtime by a #16 seed. Led by Steve Smith, the Spartans were enjoying their best season in school history in '89-'90 while Murray State, starring Popeye Jones, had come seemingly out of nowhere to capture the Ohio Valley Conference title. Jones dominated their first round matchup, scoring 37 points, but it was his teammate Greg Coble who provided the dramatics, hitting a buzzer beating three-pointer to send the game to overtime tied at 65-65. It was Frank Allen's turn in overtime for Murray State, hitting a clutch three-pointer to tie the game at 71-71, but then Michigan State's Kirk Mann hit a beautiful reverse lay-up to give the Spartans the lead for good, as they held on 75-71. Michigan State survived another tough upset bid from UC Santa Barbara in the second round before losing in overtime to Georgia Tech in the Regional Semifinals.
As for Purdue, a few heads were turned when the Boilermakers were handed a top seed in the 1996 NCAA Tournament. No doubt the team had enjoyed a fine season, but they were seen as a paper tiger in a down year for the Big 10. Though few expected them to be a realistic championship threat, no one dared to believe they may actually be toppled in the first round. Western Carolina were playing in their first tournament, having shocked Davidson to win the Southern Conference crown. After Purdue's Brad Miller missed the front end of a one-and-one with 11.6 seconds left and a 73-71 lead, the Catamounts found themselves in the position of going for a win or tie. The ball made its way to point guard Joel Fleming, whose 3-pointer looked true, but just rolled off the rim. Joe Stafford grabbed the rebound for Western Carolina and put up an off-balance runner at the buzzer to try to force overtime, but it also bounced off the rim and Purdue survived to advance. The game turned out to be more of an omen than a blip for the Boilermakers, who were upset by Georgia in the second round. Western Carolina has not returned to the tournament since, but their close call will live on forever, even after UMBC finally followed through on the impossible in 2018. As then Western Carolina coach Phil Hopkins stated after the game, in a reverse paraphrasing of John Thompson from 1989, "we didn't just deserve to keep it close, I thought we deserved to win."