#2. Kane lost his first WrestleMania match against The Undertaker
Debuting at the 1997 Bad Blood pay-per-view, Kane left a lasting impression on everyone's mind by attacking The Undertaker. The act of breaking the steel cage door with his bare hands quickly established Kane as WWE's resident monster.
At WrestleMania 14, The Big Red Machine collided with his brother in a highly-intense match. It was probably the first time someone made The Deadman look vulnerable at the Grandest Stage of Them All.
The demonic superstar proved to be a perfect match for his brother's strength. He even kicked out of the Tombstone Piledriver, making fans believe he was the one to end the streak.
Although he was stunned by Kane's resilience, The Undertaker still found a way to take down the Devil's Favorite Demon. A couple of vicious moves, followed by another Tombstone Piledriver, allowed The Deadman to topple Kane in the latter's first WrestleMania match.
#1. AJ Styles lost to Chris Jericho at WrestleMania 32
Like Kevin Owens, AJ Styles also made his WrestleMania debut in the 32nd edition of the event.
His opponent was Chris Jericho, who betrayed The Phenomenal One a few weeks ago. Although Styles already had a couple of victories over his opponent, the stakes were much higher this time.
AJ had never competed before on the WrestleMania stage, which gave Jericho an edge over his opponent. Their match turned out to be an exciting one, filled with fast-paced action and innovative reversals.
On a couple of occasions, it seemed like AJ would pull off the unthinkable by pinning the Y2J. Ultimately, Styles succumbed to a mid-air Codebreaker from Jericho, leading to his defeat.