10 WWE Superstars Who Won By Losing

6. Shawn Michaels (WrestleManias X And XI)

shawn michaels ladder
WWE.com

Despite the nickname "Mr. WrestleMania", Shawn Michaels' record at the Showcase of the Immortals is less than stellar - in win/loss column, at least. By 1994, Shawn had already lost three out of five times at WrestleMania, but his performance in the first ever (pay-per-view) Ladder Match put him on the map.

Shawn and Razor Ramon's combined efforts created one of the most iconic matches in WWE history. The match was filled with excitement, athleticism, and violence the likes of which had not been seen before in a WWE ring. Despite losing again at WrestleMania X, Michaels was the one that benefited most.

Ironically, Shawn followed up this game-changing performance by taking time away from the ring. It was a gutsy move, considering the momentum he was risking, but Michaels knew what he had accomplished at WrestleMania. He parlayed that stardom by limiting his in-ring performances over the next nine months.

It paid off. Not only did Michaels challenge for the WWF Championship at the next two WrestleManias (winning it in 1996), he was eventually labelled "the greatest in-ring performer in WWE history".

Contributor
Contributor

A former stuntman for Paramount Pictures, Matt enjoys sports, water skiing, driving fast, the beach, professional wrestling, technology, and scotch. At the same time, whenever possible. Having attended many famous (and infamous) shows including WrestleMania XV, In Your House: Mind Games, and the 1995 King of the Ring, Matt has been a lifelong professional sports and wrestling fan. Matt's been mentioned in numerous wrestling podcasts including the Steve Austin Show: Unleashed, Talk Is Jericho, and Something To Wrestle With Bruce Prichard. As a former countywide performer, Matt has been referred to as Mr. 300 for his amazing accomplishments in the world of amateur bowling. He is also the only man on record to have pitched back-to-back no hitters in the Veterans Stadium Wiffle Ball League of 2003.