10 Depressing Wrestling Retirement Matches
2. Undertaker Vs. Roman Reigns (WrestleMania 33)
The Undertaker and WrestleMania go together like beer and pretzels. His legendary undefeated streak was a key part of the 'Mania mystique for over two decades.
It was becoming obvious, though, that the Deadman was slowing down. His appearances became more sporadic, usually only involving major events.
When 'Mania 33 rolled around, it appeared clear this was to be Undertaker's last ride. His match held the main event slot and Jim Ross was brought in for commentary. It felt like a huge event, and given Reigns' mega-push, it appeared clear WWE wanted 'Taker to do the job and put Reigns over (finally.)
It didn't work.
Reigns was booed the entire match. 'Taker was nowhere near keeping up with the younger Reigns, the glory days of his epic 'Mania matches clearly gone. Before leaving defeated, Mark Calaway left his coat, gloves, and hat in the ring with a single spotlight on them, a sad yet iconic image to mark his last real solo in-ring match.
Reigns capped his win on next night's Raw, arrogantly uttering five simple words that destroyed the crowd.
Super Showdowns aside, 'Taker did have two more great appearances post-'retirement', teaming with Reigns in an awesome Extreme Rules 2019 bout and in the brilliant 2020 Boneyard Match against AJ Styles.