Round: First
Game: Richmond vs. Syracuse
Year: 1991
Watch It Here

Prior to 1991, no 15-seed had ever beaten a 2-seed since the Tournament field expanded to 64 teams. So there was certainly no reason to think that this Richmond-Syracuse matchup was going to produce anything but a blowout win for the Orangemen. However, despite a strong performance from first team All-American Billy Owens, the 'Cuse underestimated the Spiders and fell behind by eight points going into halftime. While they were able to narrow the gap, Syracuse was unable to regroup as Richmond held on for an historic four point victory.