Matt Serra def. Georges St-Pierre – UFC 69:
Heading into his match-up with Serra at 2007’s UFC 69, legendary former UFC champion St-Pierre was a nearly spotless 13-1. He had just knocked out the only man to defeat him in MMA, fellow legend Matt Hughes, to win the UFC 170-pound title in his previous bout.
But even though he was a massive dog, Serra didn’t get the memo he was supposed to go down easily. He wobbled St-Pierre with a massive overhand that put him on skates, finishing him off with strikes to complete the jaw-dropping upset victory. The win was so devastating that St-Pierre largely became a wrestling-focused fighter with a penchant for safe, controlling gameplans the rest of his career.