The 1991 Richmond team is the reason you've seen more than half of the upsets listed here on TV. 1991 was the first year CBS paid for the rights to broadcast the first round of the tourney and—after the Spiders beat the Orange to become the first #15 seed to ever beat a #2 seed—it solidified the idea to continue showing the first round in its entirety. Basically, it's because of Richmond that you need to have a "Boss Button" handy on your computer during the first round of the tourney now. God bless those Spiders!
#6. The Spiders Eat the Orange (1991)
Score: #15 Richmond 73, #2 Syracuse 69