The Biggest Losses in WrestleMania History

WrestleMania is officially just one week away. The WWE Universe is already clamoring and daydreaming about who will come out on top when next weekend’s dust finally settles in Los Angeles. 

Will new champions be crowned? Which Superstars will finally capture their own personal WrestleMania moment? Who will stand victorious at the end of each night, their hands raised in the air, fireworks going off everywhere, soaking in the adulation of nearly 100,000 fans packed into So-Fi Stadium? There will be plenty of talk on the RAW after WrestleMania about who won at WrestleMania Goes Hollywood, that’s for sure. 

RELATED: How to Stream and When to Watch WrestleMania 2023

But sometimes WrestleMania moments are measured not by who won but by who lost. Of course, wins matter in the grand scheme of things, but here are five losses that the WWE Universe will never forget!

Yeah, we can feel the memes coming already: obvious match is obvious. But we can’t have a list of the biggest losses in WrestleMania history without THE biggest loss in WrestleMania history, can we?

By now, every fan knows the story: the Undertaker took his decades-long WrestleMania undefeated streak into New Orleans against Brock Lesnar. The WWE Universe yawned as the world fully expected the Undertaker to win – until he didn’t. On that fateful night in 2014, Brock Lesnar famously became the “one” in the Undertaker’s 21-1 lifetime WrestleMania record. What is possibly more entertaining than the match itself is the crowd’s reaction to the Undertaker’s loss – a deathly pall seemed to be hanging in the arena as the WWE Universe slowly lost its grip on reality. We must admit, we’ve studied the post-match crowd footage more intently than the match itself.

When the Undertaker lost, the WWE Universe shared his pain. The Streak ended on April 6, 2014, setting in motion the eventual retirement of the Dead Man years later. It’s a match that will forever live on in infamy. 

Retirement matches are relatively common in WrestleMania lore. Some of the greatest Superstars to ever lace up a pair of boots have been forced into retirement on the Grandest Stage of Them All. Shawn Michaels and Ric Flair are inherently familiar with this particular rite of passage. 

However, it’s rare when a “loser must retire” stipulation is attached to a match between two athletes in the primes of their careers. For “Macho Man” Randy Savage and the Ultimate Warrior at WrestleMania VII, one of them would be forced into an early retirement. To say the WWE Universe was justifiably freaking out over this prospect in 1991 is an understatement. This matchup truly stands the test of time, as two larger-than-life competitors put it all on the line in arguably the most dramatic contest of the early 90s. To make matters worse: no fan wanted either man to retire, a sober fact that only added to the intense drama surrounding the match. 

In the end, Savage lost the match, relegating the once-dominant Superstar to color commentator duties on WWE television for the foreseeable future. It was considered an epic fall from grace – until Savage jumped to WCW a few years later, of course, where he once again ascended to the top of the wrestling mountain. 

This match also has one of the most unique finishes of any high-profile match ever, as Ultimate Warrior’s unorthodox method of shoulder blocking Savage out of the ring repeatedly before unceremoniously pinning him with one foot on his chest actually… worked! 

It was a match that Chris Jericho wishes he could forget. Due to a series of escalating threats and mockery by Jericho in the weeks leading up to WrestleMania, Fandango – the Superstar mostly known for his incredibly catchy entrance music – found himself in a matchup with one of the all-time greats in 2013. 

The WWE Universe was just as shocked as Y2J that he lost this match, as most fans expected Jericho to put the upstart rookie back down the pecking order immediately. But, as it turns out, Fandango had other plans. Thanks to his hybrid high-flying technical style – and a timely rollup pin – Jericho will go down in history as being on the receiving end of one of the biggest upsets in WrestleMania history. Don’t worry; this shocking loss didn’t affect Jericho’s legendary career trajectory in the long run. He scored a much-needed decisive win over Fandango at Extreme Rules 2013 to even the score between the two Superstars. 

This particular WrestleMania loss still has to hurt for Y2J!

(If you’re wondering why we didn’t embed a clip of the match up above, it’s because no official WWE clip of this particularly scathing loss exists! We’re pretty sure Jericho pleaded with WWE to take it down at one point – and succeeded.)

The buildup to Triple H and Booker T’s WrestleMania XIX match in 2003 was… controversial. 

After climbing the ranks of WWE – and finding the support of the WWE Universe fully behind him – Booker T looked poised to capture Triple H’s World Heavyweight Championship and lead the company into the future. After all, Booker T won the WCW World title on multiple occasions, and the top gold in WWE was the obvious next step in his career.

But looking back, Booker T and Triple H’s Road to WrestleMania was marred with much controversy. Triple H – firmly entrenched in the “pure evil, total scumbag villain” stage of his career – seemed to get under the skin of Booker T via many borderline racist comments towards the challenger. We won’t get into the details, but fans were dismayed that Triple H would stoop this low to get the upper hand in a rivalry. But, if anything, the WWE Universe was willing to accept this “storyline” because it meant that Booker T would eventually defeat Triple H and triumph over his dastardly rhetoric.

Except he didn’t. Booker T was Pedigreed into oblivion at WrestleMania, and Triple H – the man who once infamously told Booker T, “Somebody like you doesn’t get to be a world champion” – stood tall at the end of WrestleMania. 

It was a head-scratching moment for the WWE Universe and is one of the all-time most soul-crushing losses we wish we could change.

Long before Daniel Bryan captured the WWE Championship at WrestleMania XXX in New Orleans, he suffered one of the most embarrassing WrestleMania defeats ever in 2012. Listen, we’re not blaming AJ Lee as the reason Bryan lost in a mere 18 seconds to Sheamus – but she certainly didn’t help. Out of all the kisses in the world, we’re sure this is one Daniel Bryan regrets. 

This loss was monumental not for the moment, but for the revolution it started. Furthermore, this heartbreaking loss began an ultimate tale of redemption for Daniel Bryan that culminated at WrestleMania XXX when he finally “won the big one.” Although the WWE Universe couldn’t help but jeer and laugh at Bryan for this particular farce of a title match, little did the fans know that this was the beginning of Daniel Bryan’s ascent to greatness.

Think of it this way: if Sheamus knew the path that this loss was sending Daniel Bryan down, we think he would’ve traded places with him that day in 2012 in a heartbeat.

With WrestleMania only seven days away, we’re not exactly hoping for any current WWE Superstar to suffer these kinds of catastrophic losses – but when stakes are this high, that’s the risk these men and women have to take. 

After all, at WrestleMania, you have to risk hitting bottom to reach the top. 

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