1) #16 Princeton vs. #1 Georgetown, 1989

“The Hoyas escape, and I mean escape” was CBS announcer Billy Packer’s apt summation of this game. Three decades before UMBC became the first #16 seed to win an NCAA Tournament game, Princeton memorably came up just short. Georgetown came into this game so heavily favored that a young ESPN analyst named Dick Vitale promised to don a cheerleader outfit and serve as a ball boy for Princeton if they pulled off the upset. But coach Pete Carrill’s squad utilized their backdoor cutting offense and stout defense to take a shocking 29-21 halftime lead. 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. Hoyas center Alonzo Mourning saved the day, leading a late comeback and securing the 50-49 win with two blocked shots in the final six seconds. 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

Princeton-Georgetown became such an instant March Madness sensation that it overshadowed a near #16 seed upset from the day before. Not only did East Tennessee arguably come closer than Princeton to pulling off the improbable, they also did so against an arguably better team. Oklahoma featured All-Americans Mookie Blaylock and Stacey King, had spent most of the regular season at #1 in the AP poll, and were expected to make a second consecutive Final Four appearance. ETSU actually held the lead over the Sooners for most of the game, including by as much as 17 points in the first half. Oklahoma managed to chip away in the second half, capped by a Blaylock layup with 1:21 left serving as the winner in a 72-71 final. Oklahoma ultimately did fall short of the Final Four, losing to Virginia in the Sweet 16. The Buccaneers came back in 1992 and finally did get a major upset, taking down #3 seed Arizona.

3) #15 Georgia Southern vs. #2 Syracuse, 1987

While most NCAA Tournament games nowadays take place in NBA arenas or other neutral sites, teams would sometimes get literal home court advantage in the ’80s and ’90s. After a solid season led by All-American Rony Seikaly, Syracuse got rewarded with a #2 seed in the tournament and their first and second round games scheduled in their home site, the Carrier Dome. This first round game with Georgia Southern being so close is not just shocking in its 79-73 result but also in that the Orange didn’t really struggle. Seikaly finished with 22 points on 9-of-15 shooting while freshman sensation Derrick Coleman added 16 points and 10 rebounds. Georgia Southern just played really well themselves, especially impressive for a program making only its second tournament appearance. Seemingly locked in after the near-upset, Syracuse subsequently advanced all the way to their first National Final appearance.

4) #12 UW-Milwaukee vs. #5 Notre Dame, 2003

The 12-over-5 first round upset is a staple of March Madness, happening at least once in 19 of the last 23 tournaments. This makes #12 seeds particularly popular in bracket predictions and sometimes that can work against you. Led by rising coaching star Bruce Pearl, Wisconsin-Milwaukee looked primed to pull off multiple upsets, let alone just one, in the 2003 NCAA Tournament. Things seemed even more dire for Notre Dame when their top scorer Matt Carroll left late in the first half of this game with a sprained ankle. It was a back-and-forth battle the whole way, with Irish point guard Chris Thomas leading all scorers with 27 points. Notre Dame’s Torin Francis put his team ahead 70-69 with a layup with 32 seconds left. Milwaukee still had a chance to answer but Dylan Page’s open look at the buzzer but just missed. Perhaps taking some lessons from this disappointment, Pearl and Milwaukee returned to the tournament in 2005 again as a #12 seed, and reached the Sweet 16.

5) #14 Pepperdine vs. #3 Michigan, 1994

At 5’9″, Pepperdine’s Damin Lopez never had much of a chance in pro basketball but he put on a show to close out his collegiate career. Taking on a Michigan team that still featured four of the “Fab Five” stars (minus Chris Webber), Lopez and Pepperdine stood tall. Early in the second half, Michigan’s Juwan Howard committed a hard foul on Lopez, then stared down the diminutive guard with a glare. With the nonpartisan members of the crowd now fully on his side, both in the arena and at home, Lopez went off down the stretch. He hit five three-pointers in the second half, erasing a nine-point Wolverines lead. But Lopez’s final attempt, a potential buzzer beater in regulation with the game tied, was blocked by Jalen Rose and Michigan went on to win 78-74 in overtime. Pepperdine did not return to the tournament until 2000, when they pulled off a first round upset of Indiana. Lopez did play a little bit of pro ball in Mexico before retiring to become a coach.

6) #15 Robert Morris vs. #2 Villanova, 2010

After Hampton’s stunning upset of Iowa State in the 2001 NCAA Tournament, it took over a decade for another #15 seed to pull off a win. The most razor thin near miss came in 2010 courtesy of Robert Morris, a small private university in Pittsburgh. Villanova coach Jay Wright tied a proverbial hand behind his back by benching stars Scottie Reynolds and Corey Fisher for an undisclosed off-court infraction. Called a “teaching point” by Wright called, the benching didn’t last long but both players struggled in the game, possibly as a result. With just over four minutes left in the game, Robert Morris led by eight points when Reynolds finally shook off the rust. Just 2-of-15 from the field up to that point, the All-American point guard took control by repeatedly driving to the basket and getting fouled, then hitting 15-of-16 free throws. Villanova came back and hung on to win 73-70 in overtime. It probably wasn’t the lesson Wright intended to “teach,” but it worked out in the end, at least for one night.

7) #13 La Salle vs. #4 Seton Hall, 1992

Playing in their fourth NCAA Tournament in the last five years, La Salle was no stranger to pressure and no push over in 1992. Their first round opponent was Seton Hall, coming off a disappointing regular season after reaching the Elite Eight in 1991. While Seton Hall had an All-American in Terry Dehere, La Salle countered with MAAC Player of the Year Randy Woods. With 21 points in the first half, Woods staked the Explorers to a 36-31 lead. They extended that lead to eight points with under five minutes left in the game, when John Leahy became an unlikely hero for Seton Hall. The freshman forward came off the bench and scored nine straight points for the Pirates, then had the assist on Dehere’s game winning shot with under two seconds left. Dehere finished the game with 24 points while Woods scored 33 for La Salle in his final college appearance. The Explorers would not return to the NCAA Tournament again until 2013, when this time as a #13 seed they pulled off two upsets.

8) #15 Texas Southern vs. #2 Arkansas, 1995

Entering the 1995 NCAA Tournament, Texas Southern did have some familiarity with their first round opponent, the defending national champs Arkansas. Granted, that past experience was a 129-63 defeat against the Razorbacks during the ’93-’94 season. This game had a much different storyline, even after Arkansas opened up an early 17-point lead. Texas Southern stormed back and even took the lead themselves early in the second half. A pair of Corliss Williamson free throws put the Razorbacks ahead 79-76 with 27 seconds left but he subsequently made a major mistake on the other end, fouling Randy Bolden while the Texas Southern freshman was shooting a three-pointer. An excellent free throw shooter at 79.5%, Bolden nailed the first two but missed the third, allowing the Razorbacks to escape with a win. Arkansas won its next two games in overtime and returned to the Final Four, while Texas Southern has made five further tournament appearances and is still winless.

9) #13 Pacific vs. #4 Boston College, 2006

Nobody wanted to draw Pacific on Selection Sunday of the 2006 NCAA Tournament. The Tigers were coming off back-to-back first round wins in 2004 and 2005 and their senior laden roster seemed primed to make it a trifecta. Boston College drew the unlucky straw and even more daunting, had to travel cross country to Salt Lake City for the matchup. The game was a showdown of talented power forwards, with Boston’s All-ACC Craig Smith doing battle with Pacific’s Big West Player of the Year Christian Maraker. Smith finished with 25 points and 13 rebounds, while Maraker had 30 points, nine rebounds, and a clutch three-pointer that sent the game to overtime, capping a 13-point second half comeback. Smith responded with a pair of free throws at the end of the first overtime to tie and extend the game. Pacific’s momentum ran out in the second extra period, with Boston College scoring the first nine points and pulling away for an 88-76 win.

10) #12 Miami (OH) vs. #5 Maryland, 1985

This was a battle of two superstar juniors, with Miami’s Ron Harper going mano-a-mano with Maryland’s Len Bias. While Bias finished with an impressive 25 points on 10-of-17 shooting, Harper was undoubtedly the game’s MVP. He dropped 26 points, grabbed eight rebounds, and fueled a furious 11-point second comeback for Miami to force overtime. Late in the extra period, Harper drove the lane and threw down a posterizing dunk that not only gave the Redhawks a three-point lead, but also forced Bias to commit his fifth foul. Hitting the free throw would have effectively put the game away but Harper missed and Maryland’s Adrian Branch played the hero in Bias’ absence. Branch hit a jumper to cut the lead to one, stole the ensuing inbounds pass, then dealt the ball over to a wide-open Jeff Adkins, who laid in the game winner. Harper led Miami (OH) back to the tournament in 1986 as a senior but suffered a close first round loss for the third straight season.

11) #12 St. Bonaventure vs. #5 Kentucky, 2000

Starting in 1987, Kentucky went over two decades without losing an NCAA Tournament first round game. The closest they came during that stretch was this barn burner against St. Bonaventure. The Bonnies were playing in the tournament for the first time in 22 years and made the most of it. Kentucky held a 13-point lead early in the second half when St. Bonaventure went on a 21-4 run to take the lead. Tayshaun Prince saved the Wildcats with a three-pointer to tie the game late and when Bonnies guard Tim Winn missed a coast-to-coast layup, the fans in Cleveland were treated to free basketball. Two overtime periods, in fact, after St. Bonaventure guard David Capers hit two free throws with 0.4 seconds left to tie the game in the first overtime. Despite losing several key players to injuries during the game, Kentucky held strong in the second overtime to win 85-80. It took the Bonnies 12 years to return to the tournament, where a similar fate awaited that is detailed later in this list.

12) #15 Utah State vs. #2 Kansas, 2003

Led by All-American seniors Kirk Hinrich and Nick Collison, this Kansas team came into the tournament with Final Four or bust expectations. They eventually did make it all the way to the National Final but not before surviving a serious first round scare. Utah State never led in this game but they never fell far behind either. Kansas kept extended the lead to seven or eight points only for the Aggies to roar back and keep it tight. Utah State’s Desmond Penigar led the way with 25 points and eight rebounds, and hit a clutch three-pointer that cut the Kansas lead to 64-61 with 47 seconds left. But that would turn out to be the final basket of the game. The Jayhawks turned it over on the ensuing possession but Penigar then missed his final three-point attempt. This would turn out to be the first of five consecutive first round losses to Utah State, who finally snapped the cold streak in 2011 with an upset of Kansas State.

13) #15 Northern Arizona vs. #2 Cincinnati, 1998

Even though Northern Arizona was a #15 seed and making its tournament debut, this was a popular upset pick amongst bracket prognosticators. Northern Arizona was an experienced, feisty bunch, well coached by Ben Howland and proficient at three-point shooting. Cincinnati had built a reputation for blowing first round games and this was a risky proposition, having to travel all the way to Boise to play the Lumberjacks. Sure enough, Northern Arizona led the entire game up until the 16 minute mark of the second half, when the bigger, stronger Bearcats took over. Making full use of their size advantage, Cincinnati out-rebounded Northern Arizona 41-26, with star center Kenyon Martin grabbing 15 of his own. The game was tied in the final moments when Cincinnati’s D’Juan Baker hit the game winning three-pointer with 3.6 seconds left. Northern Arizona’s Kawika Akina’s ensuing desperation heave was short and Cincy held on for the 65-62 win.

14) #12 Iona vs. #5 Syracuse, 1998

A familiar foe awaited Syracuse coach Jim Boeheim in the first round of the 1998 NCAA Tournament. His former assistant Tim Welsh was coaching Iona and in his third season in charge, led the Gaels to their first tournament appearance in over a decade. Iona fit the classic Cinderella underdog mold in 1998, built around two starting seniors, deadly from three-point range, and confident from early season wins against Syracuse’s fellow Big East programs Rutgers and Providence. It was a back-and-forth affair as expected, with 10 lead changes taking place over the final 10 minutes of the game. Iona’s John McDonald hit a three-pointer with 24 seconds left to take a 61-60 lead. The final play from Boeheim was drawn up for Syracuse’s senior leader and top scorer Todd Burgan but when his driving shot was blocked, he grabbed the rebound and dished it outside to a wide-open unlikely hero, Marius Janulis. With 1.2 seconds left on the clock, Janulis drained it and Syracuse survived.

15) #15 East Tennessee State vs. #2 Wake Forest, 2003
16) #13 East Tennessee State vs. #4 Cincinnati, 2004

In back-to-back seasons, East Tennessee struck fear in the heart of more heralded first round opponents. They came up short each time but how memorably short it was. In 2002, the Buccaneers put up a fight against Wake Forest, shutting down their leading scorer Josh Howard. ETSU had a chance to tie the game at the buzzer but freshman Tim Smith missed a three-pointer and the Demon Deacons held on for a 76-74 win. Smith was one of four starters who returned for East Tennessee State in ’03-’04 and this time they weren’t going to catch anyone by surprise in March Madness. They took a familiar approach, once again neutralizing an opponent’s best scorer, this time Cincinnati’s Jason Maxiell. Smith once again had a chance to be the hero late but missed a lay-up with 16 seconds left that allowed the Bearcats to hang on for an 80-77 victory. Smith played two more seasons for East Tennessee but did not make a return appearance in the tournament.

“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.”

17) #13 UC-Irvine vs. #4 Louisville, 2015

For the first NCAA Tournament appearance in program history, UC-Irvine drew a team coached by Rick Pitino and two years removed from a national title. But the Anteaters were undaunted, especially Senegalese sensation Mamdou N’Diaye. One of the tallest players in NCAA Tournament history at 7’6″, N’Diaye electrified the Seattle crowd with a flurry of dunks and blocked shots. He was the literal and figurative centerpiece of a defensive battle, one in which neither team held much of a lead. With UC Irvine ahead 55-53 in the final minute, Louisville’s Wayne Blackshear drove right at N’Diaye and laid in a basket to tie the game. Quentin Snider then hit a pair of free throws to give the Cardinals the lead and they clinched it with a steal on the final play. Though Louisville advanced and continued to play, this win was later vacated due to a recruiting scandal. N’Diaye returned for his junior season but UC Irvine was unable to return to the NCAA Tournament in 2016.

18) #15 Winthrop vs. #2 Tennessee, 2006

When Tennessee returned to the tournament for the first time in five years in 2006, they were done no favors by the selection committee. The Vols were matched up against Winthrop, a well-coached (by Gregg Marshall, now the coach at Wichita State) and battle-tested team, belying their #15 seed. With multiple ties and lead changes, the game was a thrilling one until both offenses stalled late with the score tied 61-61. Tennessee’s final play was drawn up by Bruce Pearl for senior guard C.J. Watson but it ended up instead in the hands of sophomore Chris Lofton, who drilled a three-pointer with 0.4 seconds left. 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. Senior point guard Jeff Monaco blindsided Boston College with six three-pointers and finished the game with 26 points. Southern Utah led by six at halftime, when Boston College’s Troy Bell took over. Bell scored 16 of his 18 points in the second half and also grabbed nine rebounds. Rebounding really was the difference in this game, with the Eagles utilizing their size advantage to grab 29 offensive boards, a crucial asset when they shot just 32.4% from the field (including just 8-of-34 on three-pointers, 23.5%). Unsurprisingly, it was a rebound from Bell that clinched the game, grabbed after Southern Utah’s Xavier Singletary missed a shot with 13 seconds left and Boston College clinging to a 66-65 lead. Bell hit two ensuing free throws and the Eagles escaped to the second round.

20) #12 Butler vs. #5 Florida, 2000

A lot of what makes this game so special is what transpired after. Riding the momentum of Mike Miller’s buzzer beating winner to survive Butler, Florida advanced all the way to the Final Four and made the first National Final appearance in program history. Butler was seeking its first NCAA Tournament win ever but that would have to wait one more year. The Bulldogs led for essentially the entire game, with a suffocating defense hampering Florida’s drive-and-dish approach. It went to overtime, and with Butler leading 68-67 and eight seconds left in the extra period, LaVall Jordan, an 83% free throw shooter, missed two straight. Florida’s Teddy Dupay grabbed the rebound and sent it ahead to Miller, who drove straight to the basket and hit a floating jumper to give the Gators the walk-off win. Florida then dispatched Illinois, Duke, and Oklahoma State en route to the Final Four. Butler finally got its first tournament win in 2001, defeating Wake Forest in the first round.

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 actually finished the job in 1996, stunning the defending national champions UCLA as a #12 seed. They’ve been a popular bracket pool pick ever since but it’s been nothing but near misses in the last two decades. In 1997, Princeton led heavily favored Cal 29-23 at halftime but the Golden Bears were saved by future football Hall of Famer Tony Gonzalez. The two-sport star scored Cal’s final five points, including a clutch jumper that put the Bears ahead for good in the final minute. In 2011, Princeton had another chance to upset a defending champion, this time Kentucky. The score was tied 57-57 when Kentucky freshman Brandon Knight hit a driving layup to take the lead with two seconds left. Princeton’s ensuing half-court attempt was off the mark and this would turn out to be the toughest challenge of the tournament for the Wildcats, who ultimately advanced to the Final Four. Six years later, Princeton was back in the tournament and back at it again. They trailed Notre Dame with 11 points in the second half but made a late comeback and almost pulled it off, with an errant three-point buzzer beater attempt from Devin Cannady allowing the Irish to escape with a 60-58 victory.

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. If they’re playing against Duke, all the better. The Blue Devils had suffered a first round loss in 2007 for the first time ever in the tenure of coach Mike Krzyzewski, which had featured 10 Final Fours and three national titles up to that point. This stood in stark contrast to Belmont, making just its third NCAA Tournament appearance in 2008 and seeking its first win. Duke led this game by as much as 10 points in the second half but Belmont stormed back late to take a 70-69 lead. Gerald Henderson hit a clutch driving lay-up with 12 seconds left to put the Blue Devils back in the lead and Belmont was unable to answer. Four years later, the ultimate in NCAA Tournament schadenfreude finally did ensue, when Duke was 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

For the first time ever, the 2012 NCAA Tournament featured two #15 seeds pulling off first round wins, Lehigh and Norfolk State. Improbably, it happened on the same day, which also featured St. Bonaventure quite nearly joining the Cinderella fun. In their first tourney appearance since almost upsetting Kentucky in 2000 (see above), the Bonnies put a scare into Florida State. Andrew Nicholson had 20 points and seven rebounds for St. Bonaventure while the Seminoles’ top scorer Michael Snaer was 0-of-7 from the field and struggled with foul trouble. Sophomore Bernard James stepped up for Florida State, leading a 16-2 run in the second half to take their first lead of the game and seemingly put the game away. But the Bonnies were undeterred and had chances at the end to win, with a final three-point attempt from Da’Quan Cook going just awry. As of this writing, St. Bonaventure has still not won a tournament game since their 1970 Final Four appearance.

26) #14 George Mason vs. #3 Maryland, 2001

A few years later they would make their own journey to the Final Four but in 2001 George Mason almost upended Maryland’s. The Patriots were led by George Evans, a 30-year-old senior who had served several years in the U.S. Army before enrolling in college. The three-time CAA Player of the Year led all scorers in the game with 27 points and added seven rebounds and four assists. Maryland was buoyed by their star guard Juan Dixon, who scored 22 points and hit a pair of clutch free throws late to give the Terps an 83-80 lead. Those free throws came on the heels of an unfortunately timed turnover by Evans, who lost the ball out of bounds with six seconds left and sealed George Mason’s fate. The Terps advanced all the way to the National Semifinals, where they were defeated by Duke. The Patriots came back five years later and this time wreaked havoc on the bracket, upsetting Michigan State, North Carolina, and Connecticut en route to a shocking Final Four appearance.

27) #13 Valparaiso vs. #4 Maryland, 2015

13 was a lucky number for Valparaiso and their head coach Bryce Drew. In 1998, the Crusaders were a #13 seed when Drew hit one of the most famous shots in NCAA Tournament history, a buzzer beater that clinched a first round upset over Mississippi. Drew’s father Homer was the team’s coach at the time, and after a brief pro playing career, Bryce took over for his dad as Valpo coach starting in 2011. In Valparaiso’s first tournament appearance under the younger Drew, they almost repeated some of their coach’s magic. With 14 seconds left in the game and trailing 65-62, Drew called timeout. This was an opportunity to draw up a new miraculous new play to enter the annals of tournament lore. But this time Valparaiso didn’t even get off a shot attempt, with Maryland’s Varun Ram stealing the ball to ice the game. This turned out to be the second and final tournament appearance for Valparaiso under Drew, who left a year later to become head coach at Vanderbilt.

28) #13 New Mexico State vs. #4 San Diego State, 2014

From 1993 up until today, New Mexico State has lost a record 10 consecutive NCAA Tournament first round games. They came closest to snapping that streak in 2014, thanks to sophomore center Sim Bhullar. Born in Canada to Indian parents, the 7’5″, 350 pound Bhullar would brutalize opponents in the paint for the Aggies. This game was no different, with Bhullar finishing with 14 points and seven rebounds against the undersized San Diego State front line. The Aztecs’ production mostly came from guard Xavier Thames, who led all scorers with 23 points and hit several clutch shots and free throws down the stretch. SDSU led for almost the entire contest but New Mexico State made a thrilling comeback from 10 points down in the final three minutes to force overtime. Bhullar fouled out early in the extra frame, allowing San Diego State some leeway in the paint and they held on for a 73-69 win.

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

We finish with three #16 seeds who fell just short of immortality, becoming mere footnotes instead. In the first year that the NCAA Tournament expanded to 64 teams, Fairleigh Dickinson displayed the potentiality of excitement in the new format. The #16 seeded Knights stunned Michigan with their defensive intensity and held a 32-22 lead with 15 minutes to play. Roy Tarpley saved the Wolverines down the stretch, finishing with 15 points and 13 rebounds and hitting a series of clutch free throws to seal the game 59-55. Five years later, the Wolverines’ cross-state rival Michigan State made the wrong kind of history as the first #1 seed to necessitate overtime to stave off a #16 seed. Their tormentors were Murray State, whose Popeye Jones scored 37 points in the game. A buzzer beater three-pointer from Murray State’s Greg Coble forced overtime, where the Spartans held on for a 75-71 victory.

We end our trilogy with another Big-10 team, Purdue. While Georgetown in 1989 is the most infamous #1 seed near upset survivor, the Boilermakers arguably came the closest to actually losing in 1996. After Purdue’s Brad Miller missed a free throw with 11.6 seconds left, Western Carolina held the ball trailing 73-71. They called timeout and drew up a play for sophomore guard Joel Fleming, who just missed on a potential game-winning three. Western Carolina’s Joe Stafford grabbed the rebound and put up a possible game tying shot that was also just off the mark. Purdue survived but not for long, getting upset by Georgia in the second round. This was the one and only NCAA Tournament appearance in Western Carolina program history but their singular performance will never be forgotten. As then 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.”