2. Matt Serra
Matt Serra earned the right to challenge Georges St. Pierre for the Welterweight Championship after winning the Ultimate Fighter: the Comeback, a season of the series where the tournament consisted of fighters who had UFC experience already.
Hardly anyone gave Serra a chance to beat GSP at UFC 69, but that didn’t stop Serra from shocking the world and knocking him out in the 1st round. Up until Holly Holm defeated Ronda Rousey, this was the clear-cut biggest upset in UFC history, and many still claim that it is.
Unfortunately for Serra things really went down hill for him afterwards. He dropped 3 of his final 4 fights before ending his fight career to focus on his school and other projects. He’s now the voice of the UFC podcast, has a reality show with Dana White and has fighters in his camp, such as Chris Weidman, fighting in UFC main events.
After winning the title Serra lost to GSP, Matt Huges and Chris Lytle. His only victory after his big upset win over GSP was at UFC 109 when he knocked out Frank Trigg.
