#1 The Undertaker vs. Brock Lesnar (WWE WrestleMania 30)
Brock Lesnar defeated The Undertaker at WWE WrestleMania 30 in arguably the most shocking match outcome in WWE history.
"The Deadman" had won 21 matches in a row at WWE’s biggest event of the year and he was set to go 22-0 with a victory over Lesnar, but Vince McMahon changed his mind on the day of the event by selecting "The Beast" to end 'The Streak'.
Speaking on Pardon My Take in 2020, The Undertaker admitted he had reservations over the outcome because he was unsure whether the WWE Chairman was 100 percent sure that it was the right thing to do.
“It had gone back and forth. I showed up that day thinking I was going over, and it changed the day of. All I wanted to make sure was that he [Vince McMahon] had thought it all through because by that point, it was whoever was the main event then there was 'The Streak'. Those two things were the two most important things at WrestleMania.” [H/T Wrestling Inc.]
Unfortunately for The Undertaker, he suffered a concussion during the match and he does not remember anything that happened on the day of WrestleMania after 3.30 pm.