These Are the Most Heartbreaking Losses in WrestleMania History

Historically, WrestleMania has been home to some of the most triumphant moments of countlessa href="https://www.usanetwork.com/usa-insider/show/wwe-monday-night-raw" target="_blank" rel="noreferrer noopener"WWE/aSuperstars. 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,a href="https://www.usanetwork.com/usa-insider/wrestlemania-40-match-card-wwe-superstars" target="_blank" rel="noreferrer noopener"WrestleMania 40/awill 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./p pUnfortunately, 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./p pstrongFor More WWE:bra data-entity-href="https://www.usanetwork.com/usa-insider/jade-cargill-reflects-on-her-wwe-royal-rumble-debut" data-entity-title="https://www.usanetwork.com/usa-insider/jade-cargill-reflects-on-her-wwe-royal-rumble-debut" href="https://www.usanetwork.com/usa-insider/jade-cargill-reflects-on-her-wwe-royal-rumble-debut" target="_blank" rel="noreferrer noopener"Jade Cargill Reflects on Her WWE Royal Rumble Debut/abra data-entity-href="https://www.usanetwork.com/usa-insider/all-the-2024-wwe-premium-live-events-and-when-theyre-happening" data-entity-title="https://www.usanetwork.com/usa-insider/all-the-2024-wwe-premium-live-events-and-when-theyre-happening" href="https://www.usanetwork.com/usa-insider/all-the-2024-wwe-premium-live-events-and-when-theyre-happening" target="_blank" rel="noreferrer noopener"Here's When You Can Catch All The WWE Premium Live Events of 2024/abra data-entity-href="https://www.usanetwork.com/usa-insider/wwe-rhea-ripley-announces-engagement-buddy-matthews" data-entity-title="https://www.usanetwork.com/usa-insider/wwe-rhea-ripley-announces-engagement-buddy-matthews" href="https://www.usanetwork.com/usa-insider/wwe-rhea-ripley-announces-engagement-buddy-matthews" target="_blank" rel="noreferrer noopener"Rhea Ripley Breaks the Hearts of the WWE Universe, Announces Engagement/a/strong/p pToday,strongemUSA Insider/em/strongexamines 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./p div class="listicle-heading" h2span class="title"Cody Rhodes Fails to Finish the Story – WrestleMania 39/span/h2 /div p/pdiv class="embed-code-other embed-code-youtube"iframe loading="lazy" fetchpriority="low" src="about:blank" data-src="https://www.youtube.com/embed/cZASY_zwKvs?si=fhZ08lQDmW2n4Qtt" class="optanon-category-13" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen style="width: 100%; aspect-ratio: 560 / 315;"/iframe/div pWrestleMania 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!/p pIt should have beena href="https://www.usanetwork.com/usa-insider/cody-rhodes-american-nightmare-documentary-summerslam" target="_blank" rel="noreferrer noopener"the triumphant final act/aof Cody’s remarkable comeback story. Not only did he return to WWE after a prolonged absence, but he was also returning from a devastating anda href="https://www.usanetwork.com/usa-insider/wwe-hell-in-a-cell-cody-rhodes-injury" target="_blank" rel="noreferrer noopener"horrific pectoral injury/athat 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./p pIn 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 keepa href="https://www.usanetwork.com/usa-insider/roman-reigns-2-year-anniversary-undisputed-champion-wwe" target="_blank" rel="noreferrer noopener"the title around Roman Reigns’ waist/a. 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./p pThankfully, Cody Rhodes will havea href="https://www.usanetwork.com/usa-insider/the-rock-cody-rhodes-roman-reigns-drama-explained" target="_blank" rel="noreferrer noopener"a chance at redemption/ain Philadelphia in just a few weeks. Let’s cross our fingers that the same disappointing result doesn’t happen again./p div class="listicle-heading" h2span class="title"Bret Hart Loses the WWE Championship in Overtime – WrestleMania 12/span/h2 /div p/pdiv class="embed-code-other embed-code-youtube"iframe loading="lazy" fetchpriority="low" src="about:blank" data-src="https://www.youtube.com/embed/EuGdLGoG3e4?si=Vy-6WYEzJRHeQjc9" class="optanon-category-13" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen style="width: 100%; aspect-ratio: 560 / 315;"/iframe/div pSometimes, a WrestleMania moment is more heartbreaking than others, depending on who you’re cheering for in the first place./p pIn 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./p pAt WrestleMania 12, two of thea href="https://www.usanetwork.com/usa-insider/hulk-hogan-wwe-superstars-greatest" target="_blank" rel="noreferrer noopener"all-time great in-ring technicians/amet 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, anda href="https://www.usanetwork.com/usa-insider/hulk-hogan-bret-hart-hated-guts" target="_blank" rel="noreferrer noopener"Bret Hart/awas announced asemstill/emthe WWE Champion, much to the delight of millions of Hitman fans worldwide. But WWE officials had other plans – they immediately declared the matchemhad/emto 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 aa href="https://www.usanetwork.com/usa-insider/wrestlemania-2023-surprise-appearances-want-see" target="_blank" rel="noreferrer noopener"twist nobody saw coming/a./p pIt 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./p div class="listicle-heading" h2span class="title"Asuka’s Undefeated Streak Comes to an End – WrestleMania 34/span/h2 /div p/pdiv class="embed-code-other embed-code-youtube"iframe loading="lazy" fetchpriority="low" src="about:blank" data-src="https://www.youtube.com/embed/Bhqweg3Wtls?si=D3WmQqIEhSaLIY7G" class="optanon-category-13" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen style="width: 100%; aspect-ratio: 560 / 315;"/iframe/div pWe’ve written extensivelya href="https://www.usanetwork.com/usa-insider/asuka-wwe-career-explained" target="_blank" rel="noreferrer noopener"about Asuka’s surprising dominance/athat 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’sa href="https://www.usanetwork.com/usa-insider/wwe-royal-rumble-best-moments-history" target="_blank" rel="noreferrer noopener"Royal Rumble/amatch and earned a date with destiny against Charlotte Flair for the SmackDown Women’s Championship at WrestleMania 34./p pLike 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./p pUnfortunately, Asuka ran into thea href="https://www.usanetwork.com/usa-insider/charlotte-flair-break-wwe-father-ric-flair-record" target="_blank" rel="noreferrer noopener"buzzsaw known as Charlotte Flair/a, 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./p pInstead, 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./p div class="listicle-heading" h2span class="title"Booker T Falls to Triple H – WrestleMania 19/span/h2 /div p/pdiv class="embed-code-other embed-code-youtube"iframe loading="lazy" fetchpriority="low" src="about:blank" data-src="https://www.youtube.com/embed/Bhqweg3Wtls?si=D3WmQqIEhSaLIY7G" class="optanon-category-13" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen style="width: 100%; aspect-ratio: 560 / 315;"/iframe/div pLongtime 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 wieldinga href="https://www.usanetwork.com/usa-insider/triple-h-wwe-head-creative" target="_blank" rel="noreferrer noopener"behind-the-scenes political power/athanks to his real-life relationship with Stephanie McMahon. Conspiracy theorists have long maintained that Triple H wanted to bea href="https://www.usanetwork.com/usa-insider/new-wwe-world-heavyweight-championship-why-its-important" target="_blank" rel="noreferrer noopener"the World Heavyweight Champion/afor an extended period, cementing his legacy as the best ever./p pWhen 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./p pHowever, 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./p pWhen there’s a popular Reddit thread calledemTriple H Beating Booker T At WrestleMania 19 Is Still Unforgivable 15 Years Later/em, you know that the WWE Universe still isn’t over this particular WrestleMania heartbreak./p div class="listicle-heading" h2span class="title"Shawn Michaels is Forced into Retirement – WrestleMania 26/span/h2 /div p/pdiv class="embed-code-other embed-code-youtube"iframe loading="lazy" fetchpriority="low" src="about:blank" data-src="https://www.youtube.com/embed/lNBCF7AKJGA?si=c8Qaygj6JY39UBxu" class="optanon-category-13" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen style="width: 100%; aspect-ratio: 560 / 315;"/iframe/div pThe Streak vs. Career match betweena href="https://www.usanetwork.com/usa-insider/the-undertaker-names-his-dream-wwe-opponents-if-he-ever-returns" target="_blank" rel="noreferrer noopener"The Undertaker/aand 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)./p div data-embed-button="related_content" data-entity-embed-display="view_mode:node.embed" data-entity-type="node" data-entity-uuid="50b90125-5f69-46d1-ae97-2c274fbe3b4f" data-langcode="en" data-entity-embed-display-settings="[]" class="embedded-entity"h2 class="headline" a class="embed-in-feed" href="https://www.usanetwork.com/usa-insider/how-to-watch-wrestlemania-40" WrestleMania 40: How to Watch and What to Expect /a /h2 /div pThere 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./p pShawn Michaels found himself looking up at the lights after a grueling match that many maintain is one of thea href="https://www.usanetwork.com/usa-insider/main-event-match-wrestlemania-history" target="_blank" rel="noreferrer noopener"best WrestleMania main events/aof all time. The Undertaker had succeeded in ending his career./p pWas 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./p pThat’s probably why it stung so much./p pemYou can tune in to/ema href="https://www.peacocktv.com/" target="_blank" rel="noreferrer noopener"emPeacock/em/aemto watch WrestleMania on April 6 and 7. In the meantime, catch up on all things WWE Universe on/ema href="https://www.peacocktv.com/" target="_blank" rel="noreferrer noopener"emPeacock/em/aem./em/p