5) Bret Hart vs. Shawn Michaels – Wrestlemania 12
The Ironman match between Bret Hart and Shawn Michaels at Wrestlemania 12 is regarded as being one of the greatest matches in the history of this business. It’s remembered for being the match where “The Boyhood Dream” came true for The Heartbreak Kid.
What people forget in the greatest of moments for Shawn Michaels is the effect the loss had on Bret Hart. Many argue that his title loss there was the apex of The Hitman.
He took a hiatus from WWE for some time and then feuded with Stone Cold, which eventually turned him heel a year later. Eight months later, The Montreal Screwjob occurred. Wrestlemania 12 was the last time we saw that version of Bret Hart and his loss to Michaels at Wrestlemania 12 changed him forever.