10 Biggest Wins & Most Disappointing Losses For WWE’s Top Stars

Steve Austin - Biggest Win (Vs. Shawn Michaels, WrestleMania XIV)

Shawn Michaels, Steve Austin, Mike Tyson

The circumstances surrounding WrestleMania XIV were strange for more reasons than just the inclusion of Mike Tyson in the main event. Shawn Michaels had suffered a legitimate back injury in the lead up to the show, and one of 'Mania's greatest ever performers was therefore unable to give his best.

Somehow, Michaels fought through the pain barrier enough to put a red-hot Steve Austin over as the new WWF Champion. This ended the journey Austin had started upon launching his Stone Cold character in the Spring of 1996.

Now the WWF's top dog, a rampant Austin looked like a million bucks by dethroning Michaels at WrestleMania and having his hand raised by Tyson after the match. Of all the wins he would experience, that first WWF Title capture is still the biggest.

Steve Austin - Most Disappointing Loss (Vs. Kane, King Of The Ring 1998)

Kane WWF Champion
WWE.com

Mere months after becoming WWF Champion at WrestleMania and establishing himself as the promotion's biggest babyface anti-hero, it was strange to see Steve Austin lose the belt to Kane at June's King Of The Ring.

The 'First Blood' scenario felt weird to begin with due to Kane's bodysuit and mask (leaving his hand as the only exposed limb he could theoretically bleed from), and Austin's recapturing of the title the next night on Raw rendered the pay-per-view switch meaningless.

At the top of his game and a marketing machine in his own right, there's no way that Stone Cold should have lost the title so quickly, especially not to someone who would drop it right back to him 24 hours later.

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Lifelong wrestling, video game, music and sports obsessive who has been writing about his passions since childhood. Jamie started writing for WhatCulture in 2013, and has contributed thousands of articles and YouTube videos since then. He cut his teeth penning published pieces for top UK and European wrestling read Fighting Spirit Magazine (FSM), and also has extensive experience working within the wrestling biz as a manager and commentator for promotions like ICW on WWE Network and WCPW/Defiant since 2010. Further, Jamie also hosted the old Ministry Of Slam podcast, and has interviewed everyone from Steve Austin and Shawn Michaels to Bret Hart and Trish Stratus.