Where: WrestleMania 30
Winner: Brock Lesnar

Utter shock—just ask this guy. When it was announced that Brock Lesnar would be taking on the Undertaker at WrestleMania 30, most people assumed he was just going to be the next person to try and fail at beating the streak. Then, he actually did. It took three F5s, but Lesnar buried The Deadman. The immediate stunned silence of the entire crowd says it all.