1. Matt Serra def. Georges St. Pierre
UFC 69 “Shootout”
April 7, 2007 | Houston
Back in his early days, St. Pierre was aggressive and took more chances. His well-rounded talents had carried him to the UFC welterweight championship, and he looked unstoppable at 170 pounds. “Rush” was considered by some to be the closest thing to a perfect fighter, so when Serra won Season 4 of “The Ultimate Fighter” and an automatic shot at the title, the masses mostly shrugged.

Popular opinion had St. Pierre obliterating the Renzo Gracie black belt. Even though Serra said and did all the right things, the odds were stacked against him.

When champion and challenger squared off at the Toyota Center in Houston, Serra was immediately in St. Pierre’s face. The journeyman never allowed GSP to establish a rhythm, and before anyone knew it, a right hand had stunned and floored the Tristar Gym great. St. Pierre sprung to his feet but was clearly dazed. Serra tore into him with relentless punches, until another right sent the champ crashing to his back. The underdog kept firing until the fight was halted. It remains the most shocking upset in UFC history.