Recently, we looked back at the greatest Cinderella runs in NCAA tournament history. But before the underdogs can make a run to the second weekend, they first have to survive the opening round.
And that’s where the chaos begins.
The Round of 64 is where brackets get busted, legends are born, and heavy favorites suddenly find themselves walking off the floor in disbelief. From 15-seeds taking down blue bloods to the rare 16-seed shocker, these are the moments that define March.
With the madness right around the corner, let’s look back at the ten most memorable first-round upsets in modern NCAA tournament history.
16 UMBC over 1 Virginia (2018)
We have to start with the first-ever 16-over-1 upset. UMBC entered this game as a 20.5-point underdog and nearly covered as if it were the favorite. The Retrievers didn’t just beat the No. 1 overall seed, they dominated them in a way no one had all season.
Virginia went 31-3, won the ACC and had one of the nation’s best defenses. This wasn’t just historic, it was a blowout. The teams were tied 21-21 at halftime in what looked like another classic Virginia defensive grind, but UMBC took control immediately after the break.
The Retrievers shot 54% from the field and 50% from beyond the arc. Jarius Lyles led the way with 28 points and missed only three shots the entire game.
16 Fairleigh Dickinson over 1 Purdue (2023)
Five years later, Fairleigh Dickinson stunned top-seeded Purdue, becoming just the second No. 16 seed to advance to the Round of 32. The game was close all night, with FDU holding a 32-31 lead at halftime.
Zach Edey finished with 21 points and 15 rebounds, but it wasn’t enough. The teams were nearly even in field goal and free throw percentage, but Purdue’s struggles from three proved to be the difference.
15 St. Peter's over 2 Kentucky (2022)
St. Peter’s made one of the most memorable runs in recent tournament history. Led by social media sensation Doug Edert, the Peacocks advanced all the way to the Elite Eight.
Edert scored five points in the final 90 seconds of this game to force overtime, then kept delivering in the extra period. Free throws in the closing moments sealed the win, and it was fitting that Edert was the one at the line.
15 Norfolk State over 2 Missouri (2012)
Only 10 No. 15 seeds have ever advanced to the Round of 32, and few were more shocking than Norfolk State in 2012. The Spartans entered as 21-point underdogs, the second-largest upset by spread in tournament history, trailing only FDU’s win over Purdue in 2023.
Kyle O’Quinn led the way with 26 points and got plenty of help, as two teammates added 20 points each. The game was a battle throughout, with neither team able to create separation until the final moments.
Norfolk State appeared to have it sealed when Rodney McCauley stepped to the line to extend the lead, but the chaos that defines March Madness took over. McCauley missed the second free throw, a scramble for the rebound led to a jump ball, and possession stayed with the Spartans. O’Quinn then missed both free throws, giving Missouri one last chance, but the Tigers’ three-pointer at the buzzer fell short, sealing the upset.
15 Florida Gulf Coast over 2 Georgetown (2013)
FGCU’s win over Georgetown gave birth to one of the best team nicknames ever, “Dunk City.” They were as entertaining as any top seed in the field, driven by their athleticism and highlight-reel finishes, many of which came in the first round against Georgetown.
This was FGCU’s first NCAA tournament appearance and only its second year of eligibility. Sherwood Brown and Bernard Thompson led the way with 24 and 23 points, respectively.
It marked the seventh time a No. 15 seed had beaten a No. 2 seed, and it also stands as one of the largest margins of victory in that matchup.
15 Oral Roberts over 2 Ohio State (2021)
One of the few overtime games on this list, Oral Roberts and Ohio State went back and forth all night. Both teams built seven-point leads at different points, but each time the other side answered.
Kevin Obanor and Max Abmas led the Golden Eagles with 30 and 29 points, respectively, with Obanor scoring seven of Oral Roberts’ 11 points in overtime. Ohio State had a chance to tie in the final seconds, but a straightaway three-pointer missed, sending Oral Roberts to its first NCAA tournament win since 1974.
15 Princeton over 2 Arizona (2023)
This game came one day before FDU upset Purdue, making for a historic opening round in 2023. Arizona led by 12 at one point, but Princeton came all the way back behind Tosan Evbuomwan’s 15 points.
Looking at the box score, it’s hard to believe Princeton pulled it off. None of its starters made a three-pointer, and the Tigers hit only four as a team. The difference was defense. Down the stretch, Princeton forced Arizona into rushed shots and empty possessions, then closed it out with the rebound that sealed the upset.
15 Hampton over 2 Iowa State (2001)
At a time when giant upsets were far less common, Iowa State’s loss here was a massive shock. Three Hampton starters scored in double figures, led by Tarvis Williams. Williams hit a 4-foot shot with seven seconds left to give Hampton a 58-57 lead.
Iowa State’s Jamaal Tinsley had a chance to win it, but missed a layup at the buzzer, setting off a huge celebration for Hampton. The Pirates closed the game on a 14-2 run and held the Cyclones scoreless over the final seven minutes.
15 Lehigh over 2 Duke (2012)
Another game from 2012, and another reminder of how wild that opening round was. Duke entered as an 11.5-point favorite but left with a loss. CJ McCollum came off the bench for Lehigh and made a name for himself with 30 points.
Upsets happen, but what made this one stand out was Duke’s talent. The Blue Devils had eight future NBA players on the roster, including Seth Curry and Mason Plumlee, yet McCollum outscored those two combined. Lehigh won 75-70, but the result was decided earlier. The Mountain Hawks led by seven with 15 seconds left and closed it out at the line.
14 Little Rock over 3 Notre Dame (1986)
Little Rock delivered one of the first major upsets in the modern tournament, beating 3-seed Notre Dame 90-83. It came on the same day Cleveland State stunned Indiana to become the first No. 14 seed to advance, making Little Rock second in the newly expanded format.
So why do they make this list and not Cleveland State? The spread. Notre Dame entered as a 17.5-point favorite and instead lost by seven. Little Rock’s starters carried the offense, scoring all but two of the team’s points, with three players topping 20.
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