15 biggest NCAA Tournament upsets of all time

4. No. 15 Richmond over No. 2 Syracuse, 73-69 (1991, first round)

Though we’ve seen quite a few more in the past decade or so (as seen earlier in this list), a 15-seed had never topped a 2-seed as college basketball entered the 1991 NCAA Tournament. The Richmond Spiders made sure that wouldn’t be the case after that year as they took on the vaunted Syracuse Orange, led by Billy Owens and head coach Jim Boeheim.

Seven years prior, Richmond had put themselves on the map in the tournament as a No. 12 seed as they took on Charles Barkley and the Auburn Tigers. Head coach Dick Tarrant’s team didn’t melt under the pressure in that game and pulled off the upset. They weren’t done there either as they upset both Indiana and Georgia Tech in the 1988 tournament as a 13-seed to make the Sweet 16.

In the first half, the Spiders built an eight-point lead over Syracuse going into halftime. However, as we’ve seen countless times in March Madness, that lead often dissipates in the final 20 minutes of play as the higher seed simply has more talent, depth and experience. And while the Orange did win the second half, they couldn’t surmount Richmond overall, who was led by a remarkable performance from Curtis Blair, who finished the game with 18 points, six assists, three rebounds, three steals and just one turnover.

Richmond didn’t play absolutely perfect in their massive upset, but they executed their gameplan and never wavered, varying their defenses and forcing the Orange into tough situations (including 13 turnovers) all game long. In doing so, they made tournament history as the first 15-seed to record a victory.