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These Are the Most Heartbreaking Losses in WrestleMania History

Destiny had other plans for these iconic WWE Superstars at WrestleMania.

By Chris Phelan
Bret Hart in the ring

Historically, WrestleMania has been home to some of the most triumphant moments of countless WWE Superstars. From Hulk Hogan bodyslamming Andre the Giant to Seth Rollins cashing in his Money in the Bank contract to win the WWE Championship – and every moment in between – WrestleMania is where unforgettable memories happen. On April 6 and 7, WrestleMania 40 will host even more potentially iconic moments as Superstars like Bayley, Cody Rhodes, Becky Lynch, and Seth Rollins attempt to walk out of Philadelphia as champions. 

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Unfortunately, as we go down the rabbit hole of past WrestleManias, we quickly realize that not all these unforgettable memories are positive. In fact, some are downright heartbreaking.

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Today, USA Insider examines the most heartbreaking losses in WrestleMania history – the handful of times when destiny clearly had other plans for these WWE Superstars. Let’s dive in.  

Cody Rhodes Fails to Finish the Story – WrestleMania 39

WrestleMania 39 is still fresh in many fans’ minds, and we can’t even begin to think how much Cody Rhodes thinks about this fateful night!

It should have been the triumphant final act of Cody’s remarkable comeback story. Not only did he return to WWE after a prolonged absence, but he was also returning from a devastating and horrific pectoral injury that kept him out of action for the better part of a year. The American Nightmare should have defeated Roman Reigns for the Undisputed WWE Universal Championship at WrestleMania – except it didn’t happen.

In heartbreaking fashion, right when it looked like Cody was about to seal the victory, he fell into the trap countless challengers have fallen into – he underestimated how far The Bloodline would go to keep the title around Roman Reigns’ waist. The WWE Universe was ready for the coronation of a new champion – and as soon as the referee’s hand hit the mat three times, they were collectively deflated. To say the air was sucked out of the stadium that night is an understatement. Nobody saw this loss coming.

Thankfully, Cody Rhodes will have a chance at redemption in Philadelphia in just a few weeks. Let’s cross our fingers that the same disappointing result doesn’t happen again. 

Bret Hart Loses the WWE Championship in Overtime – WrestleMania 12

Sometimes, a WrestleMania moment is more heartbreaking than others, depending on who you’re cheering for in the first place. 

In the mid-90s, as a member of the WWE Universe, you inevitably had to choose between Shawn Michaels and Bret “Hitman” Hart. There was no such thing as cheering on both WWE Superstars – it just doesn’t work.

At WrestleMania 12, two of the all-time great in-ring technicians met in a 60-minute Iron Man match for Hart’s WWE Championship, and fans were collectively holding their breath for the entirety of the bout. When the 60-minute time limit sounded with neither man able to score even one pinfall on the other, the match was officially declared a draw, and Bret Hart was announced as still the WWE Champion, much to the delight of millions of Hitman fans worldwide. But WWE officials had other plans – they immediately declared the match had to have a winner and sudden death overtime was declared. This was unfair to fans of the reigning champion – overtime in a WWE match had never been seen before, and Shawn Michaels didn’t win the match during the allotted time. Talk about a twist nobody saw coming

It was a gut punch to Bret Hart and his fans. We all know how the story ends. A few superkicks later, Shawn Michaels became the new WWE Champion for the first time in his career. For Bret Hart fans, there’s nothing more heartbreaking than The Heartbreak Kid defeating your hero under bizarre circumstances.

Asuka’s Undefeated Streak Comes to an End – WrestleMania 34

We’ve written extensively about Asuka’s surprising dominance that defined her early WWE career. After competing in various Japanese promotions, Asuka arrived in NXT and steamrolled the competition. She was then promoted to the main roster, where she again dismantled every Superstar in the women’s locker room. Sporting an impressive multi-year undefeated streak, she won the 2018 women’s Royal Rumble match and earned a date with destiny against Charlotte Flair for the SmackDown Women’s Championship at WrestleMania 34.

Like Cody Rhodes at WrestleMania 39, Asuka seemed destined to become champion that night and further cement her status as one of the most phenomenal young wrestlers to ever compete in WWE – the WWE Universe was suitably pumped.

Unfortunately, Asuka ran into the buzzsaw known as Charlotte Flair, who effectively stopped her in her tracks. Not only did Charlotte successfully retain her title that night, but she did it humiliatingly from Asuka’s perspective – Charlotte made her challenger submit. This was deflating for one reason: a win against Charlotte Flair would’ve elevated Asuka to the level most Superstars can only dream of.

Instead, she became the challenger du jour to a long-running champion who won’t stop winning. We’ll be honest: between Asuka’s loss and Shinsuke Nakamura’s WWE Championship loss, it was a rough night for the 2018 Royal Rumble winners at WrestleMania 34. 

Booker T Falls to Triple H – WrestleMania 19

Longtime members of the WWE Universe know this heartbreaking loss all too well. In 2003, Triple H was firmly entrenched in what fans called his “Reign of Terror” – he monopolized the WWE main event scene, with many speculating he was wielding behind-the-scenes political power thanks to his real-life relationship with Stephanie McMahon. Conspiracy theorists have long maintained that Triple H wanted to be the World Heavyweight Champion for an extended period, cementing his legacy as the best ever.

When Booker T emerged on Monday Night Raw as the number one contender to Triple H’s championship, fans were excited. As one of the biggest stars of World Championship Wrestling in the 90s and early 2000s, the fan-favorite was finally pegged to be the WWE Superstar to dethrone The Game.

However, the buildup to their ultimately disappointing WrestleMania match was… weird. Triple H verbally and physically won their encounters in the weeks leading up to their title match, with the champion even making racially tinged comments toward his challenger. Then, Triple H decisively defeated Booker T at WrestleMania like it was nothing. Booker T fans were predictably heartbroken, enraged, and confused. 

When there’s a popular Reddit thread called Triple H Beating Booker T At WrestleMania 19 Is Still Unforgivable 15 Years Later, you know that the WWE Universe still isn’t over this particular WrestleMania heartbreak. 

Shawn Michaels is Forced into Retirement – WrestleMania 26

The Streak vs. Career match between The Undertaker and Shawn Michaels shouldn’t have surprised us. Effectively a rematch from their instant-classic encounter at WrestleMania 25, fans of Shawn Michaels were sure that The Heartbreak Kid would be the one to finally end The Undertaker’s undefeated streak at WrestleMania (which, at that time, stood at 17-0). 

There had been no rumblings that Shawn Michaels was contemplating retirement. Online chatter about the possibility that the WWE Universe would witness The Heartbreak Kid’s final WWE match was nonexistent. 

Shawn Michaels found himself looking up at the lights after a grueling match that many maintain is one of the best WrestleMania main events of all time. The Undertaker had succeeded in ending his career. 

Was the moment shocking? Yes. Was it heartbreaking? Absolutely. Do we still feel like Shawn Michaels still had a few years left in him to perform at the highest level? We sure do. 

That’s probably why it stung so much. 

You can tune in to Peacock to watch WrestleMania on April 6 and 7. In the meantime, catch up on all things WWE Universe on Peacock.

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