12 Wrestlemania Matches That Put The Undertaker’s Streak In Jeopardy

Wrestlemania is the biggest show of the year for the WWE and has been since it’s inception on March 31st, 1985. On November 22, 1990 a wrestler that went by the name of The Undertaker burst onto the scene at Survivor Series. There was an instant appeal to this seven foot athlete that felt no pain and dished out pain to anyone that he stepped inside the squared circle with.

The Undertaker has never lost at Wrestlemania and every year someone has stepped up to the plate to attempt to defeat Undertaker. 21 times wrestlers have tried and 21 times wrestlers have failed. This winning streak has become so important that it is the match that every fan wants to see and every wrestler brings their “A “game to test their skills against Undertaker.

Undertaker’s match every year is arguably the biggest selling point of Wrestlemania  because of the aura of uncertainty around it. “What if THIS is the year that the streak is broken,” is a question that is asked every Wrestlemania.

With the events of the most recent Monday Night Raw we can now pencil in Brock Lesnar vs The Undertaker for Wrestlemania 30. The Undertaker will attempt to go 22-0 at Wrestlemania, which is a feat as big as the event itself. Lesnar poses a physical challenge to Undertaker with his ruthless aggressive style that is certainly to leave a trail of devastation on the road the Wrestlemania.

12 times the streak has been in serious jeopardy of ending and what we will do here is examine the 12 times where, as fans, we didn’t know if we were witnessing the end of Undertaker’s Wrestlemania streak.


Match One: Undertaker vs Jimmy Snuka at Wrestlemania 7


Every iconic streak, from UCLA’s 88 wins in a row to Joe Diamggio’s 56-game hitting streak, had to start somewhere and Undertaker’s streak is no different. At the time, Undertaker was impervious to pain and had never competed on The Grandest Stage of Them All. WWE didn’t have any “brand equity” built into the streak or the Undertaker himself, as he headed to his first Wrestlemania to face a legend in Jimmy Snuka. While Undertaker had not scratched the surface of what he was going to be, fans wanted to see if Snuka was up for the challenge of taking down the Man from Death Valley.

The contributing factor to this match almost ending the streak was the unknown, where as fans we didn’t know how this match would go and we also had no expectations that Undertaker would win the match. Once Undertaker hit the Tombstone Piledriver on Snuka to get the pin and collect his first victory at Wrestlmania, we knew we had just witnessed the birth of a future superstar.

The thing that none of us knew on that fateful day was that we were watching the beginning of the greatest streak of professional wrestling history, which would not have been possible if Undertaker would have lost his first match.

Match Two:  Undertaker vs Giant Gonzalez at Wrestlemania 9 


Bear with me here because I believe if you were able to sit through the match itself  then you can sit through my reasoning as to why this could have potentially ended the Undertaker’s streak.

The drawing factor of Giant Gonzalez was that he was bigger and more intimidating  than the Undertaker and he was seen as a worthy challenger from a physical standpoint. As far as Gonzalez in the ring goes, well, let’s not dwell on the negatives here. This was not exactly the most visually aesthetic match Undertaker had ever been in, but that is not where the possibility that Undertaker’s streak could end would come from. Where the drama came from was that Undertaker had never look overmatched the way he was against an opponent during his short tenure in WWE.

For as limited as Gonzales was in the ring, there was still the question of HOW would the Undertaker defeat this mammoth man. Undertaker did get the win by disqualification after Giant Gonzalez used a rag of chloroform, but it was never a lock for Undertaker to win at Wrestlemania the same way it had became one as the years progressed. The streak still had no equity in it in 1993 and I doubt anyone realized at the time Undertaker was 3-0 at Wrestlemania.

Match Three:  Undertaker vs Kane at Wrestlemania 14 

Undertaker contra Kane

This was, at the time,  the most thoroughly developed and personal story line that Undertaker had been a part of. To set the back story, Undertaker’s “brother” Kane had appeared and cost Undertaker a match vs Shawn Michaels. Despite this, Undertaker refused to fight his brother Kane. Then, at the Royal Rumble that year, Kane locked Undertaker in a casket only to set the casket on fire to celebrate the “end” of Undertaker.

The build-up for this match was special because Undertaker had swore he would never lay a hand on his brother Kane and when he finally decided that at Wrestlemania it was time to exact his revenge, this would be the first time we would see them both go head to head. Kane, who was aligned with Paul Bearer, had been able to do what was since impossible and build Undertaker as a sympathetic character who was vulnerable. Kane looked as physically dominant in the ring as any opponent that Undertaker had faced up to now.

The climax of the drama came when Kane reversed the Tombstone piledriver on  Undertaker and hit Undertaker with the same Tombstone. We had all thought we saw the end of the streak, which was still not mentioned heavily at the time of this Wrestlemania. Undertaker eventually would hit Kane with three Tombstones and was declared the victor. This was a first at Wrestlemania where Undertaker, a wrestler who had in the past never looked vulnerable leading up to a big match, finally was.

Match Four: Undertaker vs HHH I at Wrestlemania 17 


HHH was the strongest heel in the business at the time. He took out legend after legend and was really cementing his name as a main event player. There was one legend that he had not taken out, however, and that was The American Bad Ass: The Undertaker. The two titans started the process on Smackdown as Undertaker came out to challenge HHH to a match at Wrestlemania and promised to make HHH famous. Undertaker did not disappoint on his promise

This was the classic match between the young and hungry lion going up against the king of the jungle, and it did not disappoint from physical and psychological standpoint. These two titans brawling all over the Astrodome was climaxed with Undertaker giving HHH a chokeslam off of a scaffolding area. HHH would show himself to be willing to pull out any stops to slay Undertaker. This was never more evident when HHH countered a Last Ride Powerbomb with hitting Undertaker in the head with a sledgehammer in a sequence of moves that at the time was fresh and exciting.

This match started the trend where wrestlers looking to make a name for themselves would want to test their skills against Undertaker at the biggest show of the year. This would add mystique to being the one wrestler to end “the streak”. Undertaker would remain undefeated at Wrestlemania by pinning HHH, but the message was clear: if you want to be the best, then wrestling Undertaker at Wrestlemania is the measuring stick.

Match 5:  Undertaker vs Ric Flair at Wrestlemania 18 

Wrestlemania 18 vs Ric Flair 

Undertaker was at the top of his game as a bad ass heel, while Ric Flair was still in a non-wrestling capacity in a General Manager role. I don’t think anyone at the time saw Ric Flair still as a wrestler because aside from Flair’s match vs Vince McMahon at Royal Rumble, Flair had not wrestled since the final episode of WCW Monday Nitro.

This feud came to light when Flair cost Undertaker a match vs The Rock at No Way Out in February. Undertaker wanted a match with Flair to get revenge on Flair, and Flair said that he wasn’t a wrestler anymore so he declined. Undertaker went after Ric Flair’s son, David Flair, attacked Flair at WWE’s training camp, and also beat up Flair’s best friend Arn Anderson in an attempt to get Flair’s attention. The match was a No Disqualification, which played into Flair’s strength as being labeled as “The Dirtiest Player In The Game”.

The core of the story was that Flair was a retired vet going against the man who had disgraced his family and with it being a No DQ match made it seem as if Flair would lay it all on the line to get his revenge against Undertaker. The highlight of the match was Arn Anderson hitting the spinebuster on Undertaker. The crowd exploded with the belief that the main two members of the famous Four Horseman would reunite in order to defeat Undertaker. It was not to be the case as Undertaker would recover to hit Ric Flair with the Tombstone Piledriver and Undertaker would run his win streak to 9-0.

Match 6: Undertaker vs Randy Orton at Wrestlemania 21 

The Undertaker 

As a young child, most kids dream about hitting the game winning home run in game seven of the World Series or even catching the game winning touchdown in the Super Bowl. In wrestling, the equivalent to that is wrestling Undertaker at Wrestlemania.

This match was the traditional young hotshot rookie in Randy Orton going up against the grizzled veteran in Undertaker. Randy Orton was in the beginning stages of his rise to super stardom and what better proving ground than Undertaker at Wrestlemania to test his merit, and boy did he with this match.

While this match in the beginning started a little slower than most would like, the ending sequence led you to believe the rookie was going to do the impossible. Randy Orton’s father, WWE legend Cowboy Bob Orton, ran in and struck Undertaker with his infamous cast only to see Undertaker sit up and seek vengeance. As Undertaker goes for the choke slam, Orton counters with an RKO out of nowhere that made fans stand up and think they were about to witness the upset of the century. This was not the case as Undertaker would reverse Orton’s Tombstone attempt into one of his own to secure the win and continue his reign of dominance at Wrestlemania.

This match, more than any match prior in Orton’s career, really showed that Orton was a believable future superstar and that he had as much ability to break the streak as any of his predecessors.

Match 7:  Undertaker vs Batista at Wrestlemania 23

Wrestlemania 23 vs Batista 

I will always hold this match in high regard because I was there to see it live and in person and as I watched the match back, JBL and Michael Cole’s work on commentary add to this match’s brilliance.

Undertaker won the Royal Rumble earlier in the year and as became customary would have the right to challenge for any title he wanted at Wrestlemania 23. Undertaker set his sights on Batista for the World Heavyweight Championship at the biggest stage in wrestling. Batista and Undertaker put on an amazing match filled with physicality that would rival two bulls running smack into each other, backing up, and running back into each other.

Batista did a great job in taking the fight to Undertaker in such a credible way and showed no intimidation stepping in the ring with Undertaker. The two would trade haymakers with the peak of the offense being Batista power-slamming Undertaker through the announce table. As Batista landed the spear-and-Batista-Bomb-combination all the fans paused with the possibility that we were about to watch the end of the greatest streak in wrestling, which is a testament to the credibility that Batista had delivered in this match . It was not the case as Undertaker responded with a Tombstone Piledriver to not only win the World Heavyweight Championship, but also steal the show against Batista at Wrestlemania 23 in a match for the ages.

Match 8: Undertaker vs Edge at Wrestlemania 24 

Wrestlemania 24 vs Edge 

This match was set for the main event at Wrestlemania with the World Heavywight Championship on the line and delivered in a way that no other Undertaker match had delivered before.  Edge had Undertaker’s number leading up to Wrestlemania and it was evident in the way the match played out. Undertaker had never defeated Edge leading up to the main event of Wrestlemania and Edge was able to use that to always be one step ahead of Undertaker during this contest which set itself about from matches prior.

It was a polar opposite from the previous years slug fest between  Batista and Undertaker. This match was a work of art from a psychology standpoint between two of the best wrestlers of any era in Edge and Undertaker. There was not one signature moment you could point to and say that THIS was the moment where the streak was in jeopardy  and that is what made the match special and different. Edge did a masterful job of countering every bit of offense Undertaker threw his way only to have the story develop into instead of Undertaker not being able to catch Edge, it morphed into Edge throwing everything he had at Undertaker only to not be able to get the job done. Edge finally tapped to Undertaker’s “Hell’s Gate” submission hold as Undertaker would regain the World Heavyweight Championship from Edge.

The streak wasn’t in trouble at one moment during this match, but this match-up sadly gets lost in the shuffle of great Undertaker matches. You will soon learn why.

Match 9: Undertaker vs Shawn Michaels I at Wrestlemania 25

Wrestlemania 25 vs HBK 

Art. Classic. Magnificent. Spellbinding.

As far as I’m concerned this match was the reason why, as a young child growing up in Nothern California. I fell in love with professional wrestling. Shawn Michaels and the Undertaker, two of the greatest to ever do this and if they’re not in anyone’s top five of professional wrestlers then I’d love to see the other four.

The buildup for this match was simple and effective, Shawn has done it all in WWE and feels he should be the guy to face Undertaker at Wrestlemania 25. What would happen next would be arguably the greatest Wrestlemania match of all time between Michaels and the Undertaker. From the beginning, Shawn did a masterful job having Undertaker chase him around the ring and catching Undertaker off guard by faking a knee injury. The cat and mouse dynamic was constant all match long with Undertakers power being a great clash of styles to Shawn Michaels quick strikes.

This match was like an emotional marathon where no man had the lead for long enough to gain any distance. Michaels did an amazing job with landing each of his multiple Sweet Chin Music kicks that allowed the audience to believe that the last kick was the one that would finally put Undertaker away. There wasn’t a move in Undertaker’s arsenal that could put away on Shawn Michaels and as great as he was in surviving the match. As Undertaker hit Michaels with what appeared to be the home run Tombstone Piledriver and went to pin a fallen Michaels only to have Michaels kick out at two, Undertaker showed a level of frustration with his facial expressions in his inability to put Michaels away. In prior matches, Undertaker’s opponents would show a level of frustration with their inability to put away Undertaker, but this was a rare match where Undertaker looked as if he didn’t know what else to he could do to put away Shawn Michaels.

The two legends would trade moves in attempts to secure the win and fans bought into the fact that the win could come at any moment for either wrestler. When Undertaker was finally able to pin Michaels after countering a moonsault into a Tombstone Piledriver, we knew we witnessed we watched one of the greatest matches ever between two of the greatest wrestlers ever.  It was special.

Match 10: Undertaker vs Shawn Michaels II at Wrestlemania 26

Ric Scuteri/AP/Press Association Images
Ric Scuteri/AP/Press Association Images

The greatest career of all-time vs the greatest streak of all-time at the main event of the biggest show of the year. I don’t think there was a better way to sell Wrestlemania than that right there.

This match had a better complete story than the match before with Shawn Michaels being tormented by the fact that he lost to Undertaker at last year’s Wrestlemania. He draws you in as a man who will do anything to erase the memory of losing to Undertaker last year. Undertaker, at this time frame, was the World Heavyweight Champion and would not accept Shawn Michaels’ challenge to a rematch at Wrestlemania. Shawn Michaels would end up costing Undertaker the World Heavyweight Championship in order to “get Undertaker’s attention”, Undertaker accepts Shawn’s challenge with one stipulation: if Shawn wins, he ends “the streak” and if Undertaker wins then Shawn Michaels career is over.

This match was different as early on Undertaker performed his signature “old school” move and appeared to to injure his ankle. This allowed Michaels to focus on that injury. Throughout the course of the match and with three separate Sweet Chin Music kicks and multiple submission attempts aimed to do more damage to that ankle really showed the depth of how far Shawn Michaels, who never has been a traditional submission wrestler, would go in order to avenge the demons of losing last year to Undertaker at Wrestlemania. While watching this match you really get the sense that Shawn will do anything to beat the streak with the belief that if he fails his career is over and that is evident in those submission attempts as well as moonsaults on the outside.

As Undertaker continues to give Shawn all that he has, you lose yourself and wonder “I don’t want the streak to end and I don’t want to see Shawn Michaels career end”.  That is the exact emotion this match draws from you and towards the final sequence of the match Shawn Michaels looks up at Undertaker a defiant superstar but he knows that he can not defeat the streak. When Undertaker hits the final tombstone to pick up the win, the overwhelming emotion is that Shawn Michaels gave his career to attempt to beat the streak and if he couldn’t do beat the streak, could it ever be done?

Match 11: Undertaker vs HHH II at  Wrestlemania 27

The Undertaker And Triple H Face Off

Nothing needed to be said on 2/21/2011, as fans we watched the vignettes for weeks leading up to that fateful day and were curious to know what they meant. As time expired we saw Undertaker appear and that more than anything was the kick off to Wrestlemania as he made his walk down the ramp on RAW we wondered where this was going. Undertaker had the ring to himself with the WWE Universe in the palm of his hand and out of nowhere HHH music played, the crowd erupted.

Two old warhorses who were battle tested and cornerstones of WWE for the last 15 years stood in the ring and did nothing but stare at the Wrestlemania 27 sign, nothing else needed to be said as the story was told without any words, they were headed on a collision course at Wrestlemania. HHH wanted to be the one to end the streak this time, and the if the last two Undertaker matches left us wondering if anyone could break the famous streak, that stare down on 2/21/2011 led us all to believe HHH would be the man to do what no one could.

This was a very different match than the previous two instant classics that Undertaker had competed in, this was a physical battle from the second the bell rang with both men trading bomb shots on the other.  The drama in this match was executed flawlessly with HHH beating Undertaker with everything from chairs to hitting countless “Pedigrees” on Undertaker in hoping to be the one to end the streak, and as Undertaker would struggle to his feet watching HHH scream at him to “stay down” added to the fact that this may be the end of the road for Undertaker. All of those moments paled in comparison to what would happen as HHH would do the unthinkable as he hit Undertaker with Undertakers signature Tombstone pile driver, crossed Undertakers arms, and attempted to gain a pin over Undertaker essentially mocking how Undertaker had defeated his opponents, we all bought in to the fact that this may be the end for NO ONE did that to Undertaker.

HHH led us all to believe he would do anything he could to end the streak and as Undertaker locked in the Hell’s Gate submission to win the match by forcing HHH to tap out, fans exhaled because they knew that no other wrestler took such a vicious fight to Undertaker before that. Undertaker had his streak extended to 19-0 but as Undertaker was unable to walk out of the arena due to the physical toll of the match fans wondered if Undertaker had won the match but had lost the war.

Match 12: Undertaker vs HHH III with Shawn Michaels as the guest referee at Wrestlemania 28

Triple H vs. Undertaker 

The end of an era and what an era it was.

This was a rarity in the sense where the match was built around Undertaker wanting revenge on a match that he was victorious in last year against HHH. Undertaker stated that he wanted to give HHH another chance at immortality and proposed a rematch between the two men at Wrestlemania 28 to settle the score. HHH, who was acting as an executive, was not interested in such a rematch because he did not want to damage the Undertaker “brand” which led to weeks of back and forth promos that culminated with Undertaker saying that Shawn Michaels was a better wrestler than HHH. This would be the breaking point of HHH as he finally accepted the challenge and stated that if they were going to do it they were going to go all the way in Hell in a Cell format.

On March 5th 2012 Shawn Michaels showed up and announced himself as the special guest referee for the Hell in a Cell match between Undertaker and HHH. It was no secret that Undertaker had retired Shawn Michaels two years ago at Wrestlemania 26 and for their respective  careers HHH and Shawn Michaels had been best friends. This would lead to a cloud of uncertainty in the air heading into the match because we were not sure if Shawn Michaels would call the match down the middle or assist his best friend HHH is doing what Shawn Michaels couldn’t do, which was end the Undertakers streak.

HHH was flawless in his attempts to do everything he could to take the fight right to Undertaker and wanting to end the streak, he would hit Undertaker with countless ruthless chair shots to Undertakers back, multiple sledgehammer blows to Undertaker, and even being able to counter Undertaker’s Hells Gate submission hold we were left in suspense the whole match that every blow could be the final blow to Undertaker. The most dramatic point in the match came where a conflicted Shawn Michaels would plead with HHH to just cover him and end the match for the physical toll Undertaker was taking was borderline inhumane, as Shawn Michaels decided to take matters into his own hands and hit Undertaker with Sweet Chin Music Undertaker fell into a HHH Pedigree, which was timed brilliantly by both men, HHH went for the cover and Undertaker kicked out at 2. The reaction on Shawn Michaels and HHH’s face told better stories than anyone else ever could, if the two best friends couldn’t work together to put away Undertaker, what would it take to end the streak?

The match ended when as HHH attempted his final pedigree only to have the Undertaker kick out, as Undertaker regained control looking to put away HHH, the closing sequence told a story of a valiant warrior in HHH who finally realized that he could not put away Undertaker and Undertaker finished HHH with a final Tombstone to go 20-0 at Wrestlemania fans exhaled and cheered watching the end of an era in more ways that could ever be described.

The most dramatic moment of the match was yet to come, as the three combatants who had carried the WWE to heights never seen before walked up the stage only to embrace at the top of the ramp. These three men looked out into the sea of 78,000 fans, seemingly in unison taking the moment in, like 3 kings looking down at the empire that they their gave blood, sweat, and tears to build. It was a visual where we knew an era was over and there were no other three wrestlers that deserved more to be there to close it out. A moment where true emotion bleeds through a television screen and you know as a fan you are watching the last time you will ever see this again, no one wanted it to end, yet we were glad it ended the way it did.

1 Comment

1 Comment

  1. MykeyLV

    February 25, 2014 at 10:29 pm

    Wow great article! Kane vs undertaker story line was always one if my favorite!

    Ive herd alot about how undertaker has been trying for years to get Brock to face him at WM so that he could retire afterwards. Wonder what the future holds to be true?

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