Top 20 most shocking first-round NCAA Tournament upsets

Bill Bender

Top 20 most shocking first-round NCAA Tournament upsets image

The NCAA men's basketball tournament – March Madness, that is – thrives on the magic of the first-round upset, those moments when Cinderella achieves that "One Shining Moment" and busts your bracket. 

No. 16 Fairleigh Dickinson had their moment on Friday. The Knights upset No. 1 Purdue 63-58 to join that list. There were two other first-round shockers in the 2023 NCAA tournament on Thursday. No. 13 Furman beat No. 4 Virginia 68-67, and No. 15 Princeton stunned No. 2 Arizona 59-55. 

Since the NCAA tournament expanded to 68 teams in 1984-85, there have been 67 first-round upsets where a teams seeded No. 13 or lower beat teams seeded 2-4 in the first round of the tournament.

  • The No. 13 seed has beat the No. 4 seed 32 times. 
  • The No. 14 seed has beat the No. 3 seed 22 times. 
  • The No. 15 seed has beat the No. 2 seed 11 times. 

Of course, UMBC made history as the first No. 16 seed to beat a No. 1 seed in 2018. 

Of course, UMBC made history as the first No. 16 seed to beat a No. 1 seed in 2018. That is the company Fairleigh Dickinson keeps now. 

MORE TOURNEY UPSETS: Nos. 67-41 | Nos. 40-21 

Most shocking first-round NCAA Tournament upsets

20. No. 14 Abilene Christian 53, No. 3 Texas 52 (2021) 

The Wildcats picked up their first tournament victory in school history in thrilling fashion against the in-state Longhorns. Joe Pleasant hit a pair of clutch free throws with 1.2 seconds remaining for the win. No. 11 UCLA beat Abilene Christian 67-47 in the second round. 

19. No. 15 Coppin State 78, No. 2 South Carolina 65 (1997) 

The first 2-15 upset on this list was a shocker. The Eagles dominated the Gamecocks behind 22 points from Danny Singletary and 20 points from Antoine Brockington. No. 10 Texas edged Coppin State 82-81 in the second round. 

18. No. 14 Austin Peay 68, No. 3 Illinois 67 (1987) 

Darryl Bedford scored 24 and Lawrence Marshall added 22 to lead the Governors past the Flyin' Illini in a shocking upset. Austin Peay lost 90-87 to No. 6 Providence in the second round. 

17. No. 13 Valparaiso 70, No. 4 Ole Miss 69 (1998)

Bryce Drew hit the impossible 3-point shot on a play that might just be the most-memorable first-round buzzer beater in tournament lore. The Crusaders beat No. 12 Florida State 83-77 before falling to No. 8 Rhode Island 74-68 in the Sweet 16.

16. No. 14 Mercer 78, No. 3 Duke 71 (2014) 

Jakob Gallon was the leader of five Mercer players who hit double figures. He scored 20 points to knock out the Blue Devils. The Bears lost 83-63 to No. 11 Tennessee in the second round. 

15. No. 13 Richmond 72, No. 4 Indiana 69 (1988) 

The Spiders knocked off Keith Smart and the defending national champions behind 21 points from Rodney Rice. Richmond also beat No. 5 Georgia Tech to advance to the Sweet 16 before falling to No. 1 Temple 69-47. 

14. No. 13 Princeton 43, No. 4 UCLA 41 (1996) 

It doesn't get much better than a back-door layup by Gabe Lewullis to knock off the defending national champions. Princeton coach Pete Carril pulled of the big upset in his 29th season as head coach. No. 5 Mississippi State then beat the Tigers 63-41 in the Round of 32. 

13. No. 15 Oral Roberts 75, No. 2 Ohio State 72 (OT) (2021) 

Oral Roberts, a 10-loss team, knocked off the Big Ten Tournament runner-up in an overtime thriller. Kevin Obanor scored 30 points and Max Abmas added 29 points in the Golden Eagles' upset. Ohio State had a chance to win in regulation, but Duane Washington missed a jumper at the buzzer. 

12. No. 15 Princeton 59, No. 2 Arizona 55 (2023) 

Princeton coach Mitch Henderson, who played on the 1996 team that upset UCLA, guided the Tigers to another shocker. Princeton beat the defending Pac-12 champions in a game that was tight from start to finish. Tosan Evbuomwan led the Tigers with 15 points. 

11. No.15 Florida Gulf Coast 78, No. 2 Georgetown 68 (2013)

Perhaps no underdog grabbed the tournament by the rim quite like "Dunk City." Sherwood Brown scored 24 against the Hoyas, and the high-flying Eagles beat No. 7 San Diego State to advance to the Sweet 16. No. 3 Florida ended the run with a 62-50 victory in that round. 

10. No. 15 Hampton 58, No. 2 Iowa State 57 (2001) 

Tarvis Williams hit the game-winner in the final 10 seconds and Iowa State's Jamal Tinsley just missed a buzzer beater. Remember Hampton coach Steve Merfield running around in the aftermath? No. 10 Georgetown ended Hampton's run 76-57 in the next round. 

9. No. 15 Norfolk State 86, No. 2 Missouri 84 (2012)

Kyle O'Quinn took over. He scored 26 points with 14 rebounds for Norfolk State to lead a shocking upset against Missouri. The Spartans lost 84-50 to No. 7 Florida in the second round.

8. No. 15 Lehigh 75, No. 2 Duke 70 (2012) 

In the same tournament, C.J. McCollum scored 30 points to lead Lehigh to a stunning first-round upset against Duke in Greensboro, N.C. No. 10 Xavier defeated Lehigh 70-58 in the next round. 

7. No. 15 Middle Tennessee State 90, No. 2 Michigan State 81 (2016) 

The Spartans were led by Denzel Valentine and were a popular pick to win the tournament, but MTSU jumped out to a 15-2 lead and never looked back. Reggie Upshaw led the Blue Raiders with 22 points. No. 10 Syracuse beat MTSU 75-50 in the second round. 

6. No. 15 Santa Clara 64, No. 2 Arizona 61 (1993) 

Steve Nash became a house-hold name with 10 points and four assists against an Arizona team that had just three losses in the regular season and featured Chris Mills, Khalid Reeves and Damon Stoudamire. The Broncos survived despite missing four free throws in the final eight seconds. 

5. No. 14 Cleveland State 83, No. 3 Indiana 79 (1986) 

This upset changed the dynamic of March Madness as we know it. Clinton Ransey scored 27 and Ken "Mouse" McFadden became a household name in the Vikings' upset of a Bob Knight-led Indiana team. Steve Alford scored 24 points in the loss. Cleveland State advanced to the Sweet 16 before losing 71-70 to No. 7 Navy.

4. No. 15 St. Peter's 85, No. 2 Kentucky 79 (2022) 

The Peacocks, coached by former Seton Hall guard Shaheen Holloway, knocked off John Calipari-led Kentucky in a first-round shocker. Oscar Tshiebwe scored 30 points and 16 rebounds, but the Wildcats were 1 of 6 from the line in overtime. Daryl Banks III scored 27 points for the Peacocks, which won its first tournament game in school history. 

3. No. 15 Richmond 73, No. 2 Syracuse 69 (1991) 

It's the first 2-15 upset in the expanded bracket era, and that gives it the edge above the rest. Curtis Blair scored 18 points for the Spiders, who then held off a Syracuse rally led by Billy Owens, who had 22 points for the Orangemen. That knocked a Syracuse team that won the loaded Big East regular season title by two games out of the tournament. 

2. No. 16 UMBC 74, No. 1 Virginia 54 (2018)

The Retrievers became the first No. 16 seed in the history of the tournament to knock off a No. 1 seed in the first round, and UMBC dominated the top overall seed in the 2017-18 NCAA tournament by shooting 12 of 24 from 3-point range. Jairus Lyles led the Retrievers with 28 points. 

FAGAN: Memories of sitting courtside when UMBC pulled its miracle

1. No 16 Fairleigh Dickinson 63, No. 1 Purdue 58 (2023) 

The Knights lost their conference championship game and had to get through a play-in game just to get a chance at the Boilermakers, who were led by 7-foot-4 center Zach Edey. Fairleigh Dickinson guard Sean Moore scored 19 points, however, and the Knights pulled off the second upset of a No. 1 seed in style. 

MORE UPSETS: Nos. 67-41 | Nos. 40-21 

Bill Bender

Bill Bender Photo

Bill Bender graduated from Ohio University in 2002 and started at The Sporting News as a fantasy football writer in 2007. He has covered the College Football Playoff, NBA Finals and World Series for SN. Bender enjoys story-telling, awesomely-bad 80s movies and coaching youth sports.