The Most Unexpected Losses Of The Undertaker's Career

Across its multi-decade history, WWE has seen several wrestlers dominate the squared circle and find great prosperity as a result. Among these individuals is the Undertaker, who swiftly became one of the most feared and dangerous individuals to ever step foot inside a WWE ring. From 1990 to his retirement in 2020, he terrified those foolish enough to cross him, bulldozed anyone who dared step in the ring with him, and took championship after championship from overzealous title holders who assumed that defeating him would be a cakewalk.

Still, for as dominant as he proved to be, the Undertaker was far from undefeated in the ring throughout his WWE run. He'd find himself on his back looking up at the lights for the three-count now and again, be it in singles or tag team competition. It was always a bit surprising to see "The Deadman" take a loss, but in most cases, it would occur in such a way that the majority of fans could see the loss coming from a mile away. However, in some rare instances, 'Taker would suffer defeat in unexpected ways that would leave WWE fans shocked long after the final bell rang.

Of the Undertaker's numerous WWE matches over the years, these loses will live on in the history books as arguably his most unexpected losing efforts.

During the second half of 1993 into 1994, the WWF Championship was in the possession of the fearsome Yokozuna. He defeated Hulk Hogan — the man who took the title from him at WrestleMania IX — for the title at King of the Ring 1993, and in the months that followed, he tore through names like Lex Luger, Crush, and Bret "Hitman" Hart. Sadly for him, by the start of 1994, he wound up opposite the Undertaker, who desired to take the WWF Championship for himself and strike fear into his heart by any means necessary. The two powerhouses would meet at the 1994 Royal Rumble event.

To build intrigue around the match and give 'Taker a psychological edge over Yokozuna, their clash became a casket match. The only way it would end is when one man was tossed in a ringside casket with the lid shut over them. Aware of the uphill battle his client was in, Yokozuna's manager, Mr. Fuji, enlisted the help of Bam Bam Bigelow, Diesel, Adam Bomb, Jeff Jarrett, and more to take out the Undertaker. It took 10 men to lay him out in the center of the ring, making it easy for Yokozuna to place him in the casket, shut the lid, and win the match. 'Taker wouldn't appear on WWF programming again until August, though before he left, he'd let WWF fans know via the Titantron that he had no intention of resting in peace.

On paper, one had to imagine that the Undertaker would defeat Yokozuna with ease in a casket match. After all, he was practically immune to pain and was beginning to make the stipulation one of his signatures. Evidently, all of Yokozuna's unexpected helpers ensured a loss no one could've seen coming.

At WrestleMania 13, the Undertaker met Sycho Sid in a main event encounter for the WWF Championship. After a back-and-forth battle between these two behemoths, "The Deadman" held the championship high to close out the landmark event. With that, his dark reign atop the WWF mountain began, which saw him defeat such challengers as Mankind and Vader as 1997 unfolded. Come SummerSlam in early August of that year, Taker would have to defend his title against "The Best There Is, The Best There Was, And The Best There Ever Will Be," Bret "The Hitman" Hart, in the main event.

Further complicating a match where he had to put his title on the line against one of the WWF's most gifted in-ring stars, the Undertaker had to deal with a special guest referee in the form of "The Heartbreak Kid" Shawn Michaels. He and Hart had continued their bitter feud heading into the bout, making 'Taker more of an afterthought in the overall story. Nevertheless, Hart was determined to take the championship, putting up a fight only he could. The Undertaker battled back in the name of the WWF Championship, but sadly, he couldn't quite cinch the victory thanks to HBK.

At the end of the match, Bret Hart grabbed a chair and attacked the Undertaker with it. A furious Shawn Michaels took the weapon from him and began berating him, prompting Hart to spit on him. Michaels swung the chair, Hart ducked, 'Taker took steel to the skull, and Hart used the miscalculation to score the pinfall. Talk about an unexpected finish.

Shawn Michaels' retirement match against the Undertaker at WrestleMania XXVI was the perfect send-off for "The Showstopper." He rode off into the sunset before he could become a parody of himself, and for a while, it seemed like he'd actually stay retired. However, in 2018, Triple H and the Undertaker found themselves in one last in-ring feud that started at Super Show-Down. "The Game" won the match, but the war between himself and "The Deadman" was far from over. In the weeks that followed, he and Michaels reformed D-Generation X to oppose 'Taker and his demonic sibling, Kane.

In a match no one expected to see in 2018, DX and the Brothers of Destruction met at Crown Jewel in a tag team match. Give the advanced age of all four men, and the fact that Michaels hadn't wrestled in nearly a decade, fans were skeptical of this bout from the beginning. Sure enough, it was an absolute disaster. Triple H tore his right pectoral early in the match, Kane's mask fell off during a scrap with Michaels, and one botched move after another occurred. Triple H's injury left Michaels to fend for himself for much of the match, which many were surprised dragged on as long as it did.

Somehow, some way, Shawn Michaels and an injured Triple H got the better of the Undertaker and Kane at Crown Jewel 2018. This match deserves to be forgotten, though one can't help but scratch their heads over the Brothers of Destruction's loss here. They had D-Generation X on the ropes for nearly the entire match, yet they couldn't get the job done.

In early 2006, "SmackDown" viewers got their first look at a mountain of a man known as the Great Khali. Standing well over seven feet tall and weighing around 400 pounds, "The Punjabi Nightmare" was practically tailor-made for professional wrestling based on his look alone. Was he the most graceful or technically gifted competitor to ever enter a WWE ring? Certainly not, but that didn't stop him from making a beeline for one of his real-life inspirations, the Undertaker, upon debuting on the main roster and giving the ring general a run for his money. They met in a sanctioned match for the first time at Judgment Day 2006.

Ahead of Judgment Day, the Great Khali made his in-ring debut on April 17 edition of "SmackDown" and made quick work of Funaki. From there, he crushed Rey Mysterio, Matt Hardy, and Scotty 2 Hotty in preparation for his bout with the Undertaker. When he and "The Deadman" finally met, the latter did his best to chop his massive opponent down to size. However, Khali's power and the intervention of his manager, Daivari, proved too much for "The Phenom" to handle. In under 10 minutes, Khali defeated the Undertaker, leaving fans to wonder if anyone out there could stop his reign of terror.

The Undertaker later got his revenge on the Great Khali, and as time went on, he slipped further and further down the card. Khali turned out to be yet another failed WWE main event experiment — one that caught 'Taker, of all people, in the crossfire. 

Heading into the 2010 edition of Elimination Chamber, the World Heavyweight Championship was in the possession of the Undertaker. He defeated CM Punk for the title at Hell in a Cell 2009, and had no desire to let it go. Thus, he walked into the Elimination Chamber match more than prepared to take down Chris Jericho, John Morrison, R-Truth, CM Punk, and Rey Mysterio so he could walk into the following month's WrestleMania XXVI as champion. Not only did his own pyro infamously burn him during his entrance, but he didn't ultimately leave St. Louis, Missouri's Scottrade Center with the World Heavyweight Championship.

For the better part of the match, it seemed like the Undertaker would successfully defend his title. One by one other competitors were eliminated, until it came down to 'Taker and Jericho. As he closed in on victory, "The Deadman" was blindsided by Shawn Michaels, who surprised everyone by sneaking into the match via a floor grate. One Sweet Chin Music later, and "Y2J" was the new World Heavyweight Champion. Michaels' interference came as a result of his need to face 'Taker at WrestleMania XXVI, since he felt he had to take him on at "The Show of Shows" one more time to make up for his loss at WrestleMania 25 the previous year.

So ended the Undertaker's final title run in WWE and his final Elimination Chamber match. He went on to face and defeat Shawn Michaels at WrestleMania XXVI, ending his career in an astounding match. Had it not been for his shocking Elimination Chamber 2010 loss, though, this historic bout could've been for the World Heavyweight Championship.

As the Undertaker wound down his wrestling career, his time on WWE programming diminished significantly. For the most part, he'd only appear during WrestleMania season, building a feud with a given in-ring icon or rising star that would culminate in a match at that year's event. When the road to WrestleMania 33 began, however, 'Taker sought to take a much different route to "The Show of Shows." He entered the 2017 Royal Rumble match with his eyes set on a world championship match at WrestleMania, though this plan would fade into oblivion thanks to one man: Roman Reigns.

Angered over Reigns eliminating him from the Royal Rumble and his claims that WWE had become his yard, the Undertaker challenged the former Shield member to a match at WrestleMania 33. Reigns accepted, and even though there wasn't a title on the line, this was the night's main event. Unlike many of his previous WrestleMania performances, "The Deadman" couldn't put Reigns away with ease. "The Big Dog" brought the fight to his supernatural opponent, and after a litany of spears and Superman punches, he pinned the Undertaker in the center of the ring.

As WWE fans looked on in shock, the Undertaker left his gloves, hat, and coat in the ring to close out the show. It seemed that this was his final goodbye from WWE, which, of course, wasn't at all the case — likely due to his disappointment in the overall match. Still, seeing 'Taker lose in such decisive fashion for the second time at WrestleMania of all events was surprising to witness.

The night after WrestleMania XII, WWF fans met a frightening new character known as Mankind. This leather mask-clad entity squashed Bob "Spark Plug" Holly in his first televised "Raw" match in the promotion, employing a brand of ferocity WWF viewers hadn't seen before from anyone on the roster. From there, he wasted little time moving on to a feud against someone who'd become one of his biggest rivals: the Undertaker. The two crossed paths a few times as the months went on, though their first actual match didn't take place until SummerSlam 1996 — the first-ever Boiler Room Brawl in WWF history.

As the name implies, Undertaker and Mankind's match began within the confines of a boiler room before spilling to other locations inside the arena. The match would only end when one of the competitors secured the enigmatic urn held so dearly by 'Taker's longtime manager, Paul Bearer. Having used all kinds of weapons and dangerous moves against each other in locations where no human being should wrestle, they inevitably made their way to the ring. At this point, it appeared that "The Demon of Death Valley" had the match in the bag, but then the unthinkable happened. Bearer turned on him and aligned with Mankind, offering him the urn and therefore the victory.

Through the remainder of the 1990s, Mankind and Undertaker's rivalry continued and the latter's relationship with Paul Bearer fluctuated. Nevertheless, nothing could wash away the shock of seeing Bearer turn his back on 'Taker, causing "The Deadman" to lose and leaving him on his own in the WWF for the first time.

The Undertaker made his now-legendary debut at Survivor Series 1990, helping the Million Dollar Team (Greg Valentine, Ted DiBiase, and the Honky Tonk Man) defeat the Dream Team (Dusty Rhodes, Bret Hart, Jim Neidhart, and Koko B. Ware). Just over a year later at Survivor Series 1991, he captured his first of many WWF Championships in a hard-fought match against the undeniable face of the company, Hulk Hogan. With the sinister Paul Bearer at his side — the replacement for 'Taker's first WWF manager, Brother Love — it seemed like he was ready to embark on a lengthy, dominant title reign.

The Undertaker's first televised WWF Championship defense took place at the This Tuesday in Texas event against none other than Hulk Hogan. The two future WWE Hall of Fame inductees battled it out for just over 13 minutes, and when it was all said and done, the theory that 'Taker would enjoy a long run as champion was proven woefully and surprisingly incorrect. As a result of a "Nature Boy" Ric Flair run-in, a handful of ashes thrown into the Undertaker's eyes, and a tight roll-up, Hulk Hogan left the Freeman Coliseum in San Antonio, Texas as WWF Champion once more.

It's baffling that after building the Undertaker up as a near-unstoppable monster, the WWF brass only allowed him to hold onto the WWF Championship for less than a week. Although, one can't help but wonder if Hulk Hogan's claim of the up-and-coming 'Taker hurting his neck during their first title match dashed his chances at a longer reign. Regardless, what's done is done.

At the Battleground event in 2015, he set his sights on his WrestleMania XXX opponent and the man who ended his WrestleMania undefeated streak, Brock Lesnar, reigniting their feud heading into SummerSlam. The two ring titans clashed at "The Biggest Party of the Summer," with Taker narrowly securing the win.

As SummerSlam slipped further and further into the past, Lesnar and the Undertaker kept their rivalry alive. They'd meet once again for what would turn out to be the final time at Hell in a Cell in October of 2015. "The Beast Incarnate" and "The Phenom" duked it out inside the steel structure, throwing caution to the wind as they pursued ultimate victory in this blood feud. To finish off the Lesnar-'Taker saga, it would make sense for the latter — especially under one of his signature match stipulations — to score the victory. However, in a surprising turn of events, Lesnar won with a low blow and a third F5.

Seeing as the Undertaker came back to get even with Brock Lesnar and his manager, Paul Heyman, after Lesnar snapped his WrestleMania undefeated streak, one would imagine he'd walk away from their Hell in a Cell encounter as the winner. He'd give Lesnar his comeuppance and send the fans home happy. Evidently, that's not the way fate wanted their rivalry to pan out.

The Undertaker had a chance to kick-off another WWE Championship reign at No Mercy 2003 when he met champion Brock Lesnar in a biker chain match. However, he didn't count on the interference of Mr. McMahon, who stuck his nose where it didn't belong and ensured Lesnar held onto the title. Understandably angry, 'Taker used his rage to defeat Lesnar and the Big Show in a handicap match on "SmackDown" that, if he won, would allow him to choose his opponent for Survivor Series. Not long after having his hand raised in victory, he let McMahon know that he had a match against him at the November pay-per-view staple.

It's no secret that, even though he's entered the ring more than a few times, Vincent Kennedy McMahon is no professional wrestler. He's not one to pump out five-star classics or technical clinics. In fact, he's only really good for taking a beating, and at Survivor Series 2003, take a beating he did. The Undertaker absolutely demolished McMahon, rendering him a bloody mess mere moments into the bout. To make matters worse, this was a Buried Alive match, meaning that either he or, by some serious divine intervention, 'Taker, would have to be tossed in a grave and covered in dirt to end the match.

While it was far from divine — in fact, it was quite the opposite — Mr. McMahon was indeed saved by an intervening party. Out of nowhere, Kane emerged and began attacking the Undertaker, leaving him into a pre-dug grave and practically spoon-feeding McMahon the win. While shocking in the moment, it all made sense, as the build for Taker and Kane's match at WrestleMania XX began in the aftermath.

Remember that loss at SummerSlam 1997 that caused the Undertaker to lose the WWF Championship to Bret Hart? Well, it should come as no surprise that he didn't let Shawn Michaels off easy for that blunder. Taker continued to keep one eye on Michaels and the other on the WWF Champion, culminating in a match between him and "The Heartbreak Kid" at the In Your House: Ground Zero event to determine who would become the number one contender. The match ended in a double disqualification, so instead of giving both or neither of them a title shot, they'd have a rematch for the number one contendership at In Your House: Badd Blood.

To prevent any outside shenanigans, the Undertaker and Shawn Michaels met inside Hell in a Cell — the first appearance of the structure in WWF history. This massive, threatening cage seemed like a second home to "The Deadman" in no time, and that only grew more apparent as he used it to annihilate "HBK." The bloodied Michaels took nasty bump after nasty bump, even falling from high up on the outer wall through the announce table. Suffice to say, it looked like 'Taker versus Hart was all but confirmed for Survivor Series 1997. That is, until the lights went out.

Under red lights and surrounded by flames, WWF audiences got their first look at Kane: the Undertaker's brother once thought to be dead who Paul Bearer had promised to bring to the WWF in weeks previous. The red and black-clad monster tore the door off of the Hell in a Cell structure, hit his sibling with a Tombstone Piledriver, and left Shawn Michaels with a winning opportunity. Losses don't get much more unexpected than that.

When looking back on the Undertaker's WWE legacy, it's impossible not to bring up his WrestleMania undefeated streak. Beginning in 1991 with his victory over Jimmy "Superfly" Snuka at WrestleMania VII, Taker would make "The Show of Shows" his stomping ground as the years went on. Shawn Michaels, Ric Flair, Triple H, CM Punk, and more all failed to defeat him at the event, instead adding their names to the long list of foes "The Deadman" overcame at WWE's biggest event of the year. By early 2015, his streak had extended to a staggering 21-0, and it stood to reason he'd retire undefeated.

It was business as usual heading into WrestleMania XXX, with the Undertaker returning to WWE programming to build a feud against his would-be opponent at the pay-per-view. For the first time ever, he and Brock Lesnar would square-off at WrestleMania, and when the night came, "The Beast Incarnate" didn't hold back. He wasted no time bringing the fight to 'Taker (who turned out to be concussed for much of the match), and while "The Phenom" fought hard, he couldn't fully swing the momentum in his favor. With one final F5 into a pinfall attempt, fans everywhere expected your typical dramatic near-fall, as was tradition in streak matches.

Not this time. 

Brock Lesnar successfully pinned the Undertaker clean at WrestleMania, making his opponent's record 21-1. In the immediate aftermath, a hush fell over the thousands of fans in attendance at the Mercedes-Benz Superdome in New Orleans, Louisiana as everyone tried to comprehend what had just happened. With Lesnar gone, a shaken Taker got to his feet and the crowd gave him a well-deserved standing ovation. On this night, history was made, and the Undertaker was handed the single-most unexpected loss of his entire career.