27. “The Olympic Hero” Kurt Angle
The Olympic Gold Medalist himself first defeated the legendary Undertaker in the Co-Main Event of the ‘WWF Survivor Series 2000’ PPV, thus successfully defending his WWF World Title. Almost 2 years later on June 18, 2002 he would beat Taker again during an episode of SmackDown!.
Another huge victory for Kurt came in the Main Event of the ‘WWE No Way Out 2006’ PPV, where he defeated the Deadman clean in a great 5***** match.
