#1 The Hurricane def. The Rock (WWE Monday Night RAW March 10th 2003)
Arguably The Rock's most infamous upset defeat came at the hands of The Hurricane on Monday Night RAW in 2003.
The Rock returned to WWE in 2003 with a new heel "Hollywood" character. The Great One was no longer The People's Champion and was instead a cocky, arrogant, villianous movie star.
During the build to The Rock's match with Stone Cold Steve Austin at WWE WrestleMania XIX, The Hurricane would regularly participate in hilarious backstage segments with The Rock on Monday Night RAW.
The Rock would openly mock The Hurricane for pretending to be a superhero, questioning what Hurricane's superpowers truly were and if The Hurricane could even fly. This led to RAW General Manager Eric Bischoff setting up a match between The Rock and The Hurricane in the main event of Monday Night RAW.
The match between The Rock and The Hurricane was a completely one-sided affair, with the former WWE Champion making quick work of his opponent, mocking him in the process. The Rock even put on The Hurricane's green cape to mock WWE's resident superhero.
However, as The Rock was set to finish off The Hurricane with The People's Elbow, Stone Cold Steve Austin's music hit to a thunderous ovation from the WWE Universe.
The Texas Rattlesnake made his way down to ringside and locked eyes with his WrestleMania XIX opponent. The Rock, distracted by Stone Cold Steve Austin at ringside, was then shockingly rolled up by The Hurricane for the pinfall victory in one of the biggest upsets in the history of Monday Night RAW.