Mike Tyson vs. Buster Douglas

February 11, 1990 HBO Broadcast Tokyo Dome Tokyo, Japan Widely considered the biggest upset in sports history. Douglas entered the fight as a 42-1 underdog. Tyson would be dominated the entire fight until the 8th round when he knocked Douglas down, leading to the infamous long count controversy. Douglas would recover and eventually score a 10th round KO to capture the undisputed heavyweight championship, handing Tyson his first career loss.