#4. Roman Reigns - WrestleMania 33
Had Roman Reigns turned heel post-WrestleMania 33, this wouldn't have even been on the list. This would be the third straight WrestleMania main event for Roman Reigns - and the third straight legend he would face at The Grandest Stage of Them All.
When it was revealed that the non-title match between Roman Reigns and The Undertaker would headline WrestleMania 33, one thing seemed clear - this would be The Undertaker's final match in WWE.
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Nobody objected to the idea of The Undertaker retiring, and under those circumstances, Roman Reigns winning made a lot of sense. There were two big problems - first, WWE didn't do well to capitalize on Roman Reigns' win, and this wouldn't be The Undertaker's final match.
He would go on to wrestle a few more times, including a match in 2019 where he teamed up with Roman Reigns to defeat Drew McIntyre and Shane McMahon.
Given that The Undertaker would only retire three years later, he would likely have been better off winning the match against Roman Reigns. Many would argue that The Undertaker shouldn't have even competed at WrestleMania that year because of his weak physical state.