Who could have ended The Undertaker’s Streak? – Part 4

Who could have ended The Undertaker’s Streak? Part 1 – Part 2 Part 3


For 20 years the Undertaker has seen Superstars come and go from the WWE. All have tried to stake their claim, but none have been able to outlast the Phenom. The WWE ring is truly his yard.

Throughout his time in the WWE, the Undertaker has amassed heaps of fallen victims. The most recognizable of these heaps are his Wrestlemania opponents. Three WWE Hall of Famers have fallen victim to the Undertaker’s impressive Wrestlemania streak. Several future WWE Hall of Famers have also bowed in defeat to the Streak.

The list of fallen foes is 17 Superstars long. Of these 17 Superstars, who had the greatest upper-hand on the Undertaker during their match? Who was only a second away from pinning the Deadman’s shoulders for the three-count?

Who could have ended the Streak?

Hindsight is always 20-20

Before I continue, I’d like to point out that my opinions are based on my after-the-fact knowledge and thoughts. For some matches, I have a greater knowledge of the entire feud, others not as much. This fact probably isn’t ideal for something like this, but this is my blog and my opinion.

The 25th Anniversary of Wrestlemania – XXVII

vs. Shawn Michaels
The 25th Anniversary of Wrestlemania, April 5, 2009

“Sometimes, it’s hell getting to Heaven.”

— The Undertaker

Just as the Undertaker was returning from a hiatus, Shawn Michaels found himself  in a feud with JBL. Michaels was in financial trouble, catching wind of this, the money-savvy JBL took advantage and presented HBK with an employment opportunity. With no other choice to provide for his family, Shawn Michaels swallowed his pride and accepted JBL’s proposal.

At the 2009 Royal Rumble, Michaels was instructed to help JBL defeat John Cena, which would allow him to win the World Heavyweight Championship title. Just before the match began, JBL met Shawn Michaels in the dressing room and antagonized him. Ready to follow JBL’s orders and accompany him to the ring, the Heartbreak Kid turned and came face-to-face with the Deadman. It was then that The Undertaker’s uttered the words that would help define a truly amazing Wrestlemania match.

Shawn Michaels was unable to help JBL capture the big, gold belt, which lead to Shawn Michaels and JBL at No Way Out, with the stipulation of “All or nothing;” if Shawn won, he’d be let go of his year-long deal with JBL; he won. Now free of his contract with JBL, Shawn Michaels set his sights on the ‘granddaddy of them all’ – Wrestlemania 25. Unsuccessful in his match, The Undertaker was unable to win the Smackdown! Elimination Chamber match, leaving his Wrestlemania card open.

Following the No Way Out pay-per-view, JBL announced on RAW that it was his destiny to defeat The Undertaker’s Wrestlemania streak. Shawn Michaels came out to the ring and said he disagreed and believed that instead he would be the one to take out The Undertaker at Wrestlemania. They fought the following week to decide who’d be the one to step up to the impressive Streak, and once again, Shawn Michaels proved the better man and beat JBL. Wanting to make his own Wrestlemania moment though, Vladmir Koslov also wanted to take on the Streak, but again, Michaels defeated his opponent and was granted a match against The Undertaker at Wrestlemania.

Once The Undertaker officially accepted HBK’s offer, the mind games begun. This time though, the tables were turned on The Phenom. Shawn Michaels was the one playing games. Like every other time the two had met in the past, Shawn Michaels kept his guard up and had the Deadman’s number in the weeks leading up to the ‘Show of Shows.’ In a tag team match on Raw, Shawn Michaels stole the pin from The Undertaker, his partner, and dashed up the ramp and backstage before The Undertaker could get his hands on him. The Undertaker would stop at the top of the ramp to look back at the ring, and as he turned back around, Shawn Michaels laid him out with a Superkick. Before the two legends could face off at Wrestlemania, Shawn Michaels was determined to show the bigger man that he was not scared of The Undertaker. On an episode of Smackdown!, Shawn Michaels appeared, dressed in a white outfit, similar to The Undertaker’s. He said although The Undertaker was undefeated at Wrestlemania, he was Mr. Wrestlemania, and he also quoted scripture, saying:

“In the beginning darkness moved across the face of the deep and God said, ‘let there be light,’ and there was light; and God saw the light and that it was good. He divided the light from the darkness; He called the light day and the darkness night. Yea, though I walk through the valley of the shadow of death, I will fear no evil. I have victory over death, Hell and the grave. Undertaker, I have eternal light.”

— Shawn Michaels

The Undertaker tried to gain the upper-hand on Michaels, tearing through the ring and trying to pull Shawn down underneath, but  Michaels was able to escape his grasps. Shawn Michaels then held a funeral for The Undertaker and his streak, trying again to get the best of Michaels, but again he failed in his efforts. As the lights went off, signaling his emergence, and came back on, HBK was no where to be found. The Undertaker opened the casket in the ring, thinking Michaels was hiding there, but to his frustration, he wasn’t. He turned around and Michaels came out from under the casket and proceeded to Superkick The Undertaker again.

Shawn Michaels descended from the heavens, The Undertaker rose from the dark depths and the two took to battle in the squared circle at the 25th Anniversary of Wrestlemania.

During the opening minutes of the match, Michaels was able to elude The Undertaker’s strikes, using his quickness to his advantage. Soon though, The Undertaker gained the advantage, going Old School on Michaels. After feigning a knee injury of his own, Michaels took to taking out the Phenom’s. His efforts proved successful as throughout the rest of the match, The Undertaker’s knee gave out on him several times.

After sideswiping a huge moonsault by HBK, The Undertaker rolled back into the ring and then went for his patented Suicide Dive. Mr. Wrestlemania caught sight of his intentions and was able to pull a camera man into The Undertaker’s flight path. Nearly breaking his neck upon landing, The Undertaker stay laid out as Michaels made his way back into the ring, dragging the referee with him to count out The Phenom. With only a second to spare, The Undertaker miraculously made it back into the ring. Shawn started to tune up the band to finally put The Undertaker to rest, but ‘Taker countered with a Chokeslam. After a series of finishers and counters from both men, The Undertaker went to the top rope for an elbow drop, but Shawn rolled out of the way. Unable to pin The Undertaker after multiple Superkicks, Shawn Michaels went to the top rope for another moonsault, hoping for better results, but The Undertaker caught him mid-air and delivered yet another Tombstone to the Showstopper and finally got the 1-2-3.

The Verdict

Every single word that I’ve just written about ‘Taker-Shawn I, does absolutely no justice to how truly spectacular their ‘live-action work of art’ was. It, as well as it’s successor, was breath-taking. The fans were on the edge of their seats the entire time. The Showstopper and The Phenom proved, beyond a shadow of doubt, why they are the greatest WWE Superstars of all-time.

As for the winner of the match, I believe everyone was a winner. A better match, between two better competitors on a grander stage wouldn’t be possible. It doesn’t get any better than The Undertaker and Shawn Michaels.

While fans were split between the two Superstars, The Undertaker did indeed advance his undefeated streak to 17-0. In my eyes, there was never any doubt of this. Like Ric Flair before him, Shawn Michaels’ career and accomplishments speak for themselves. There was absolutely no need for him to win the match; it would have been a waste to give such a huge accomplishment to someone whose list of accomplishments is a mile long. Shawn Michaels didn’t need to win.

The Undertaker – 17-0

vs. Shawn Michaels
Wrestlemania XXVI, March 28, 2010

Following their epic encounter at The 25th Anniversary of Wrestlemania, both Shawn Michaels and The Undertaker took a brief hiatus from in-ring action. Shawn returned to reform Degeneration X with Triple H and The Undertaker returned to battled against the Straight Edge Superstar CM Punk.

At the annual Slammy Awards on Raw, when accepting their Slammy for Match of the Year, Shawn Michaels said he was proud of what they’d accomplished and the history they were able to write, but just as he was leaving, he proclaimed that he could beat The Undertaker. He then challenged The Undertaker to a rematch at Wrestlemania 26. The Undertaker though, refused the offer. Shawn Michaels took it upon himself to earn the right to face The Undertaker, who was the World Heavyweight Champion at the time.

He entered the Royal Rumble in hopes of outlasting 29 other men, but he was eliminated by Batista. Losing his composure, he then attacked a referee. His next to meet The Undertaker at Wrestlemania was to enter and win the Elimination Chamber, but he failed to qualify for the match after losing to Randy Orton. He made his presence known though, climbing out from under the chamber and Superkicking The Undertaker, costing him his title against the final chamber participant, Chris Jericho.

The following night on Raw, The Undertaker finally agreed to give Shawn his rematch, but he then said HBK’s soul wouldn’t be enough, he had to put up his career against The Undertaker’s Streak. The Heartbreak Kid accepted by telling The Undertaker he didn’t understand… if he couldn’t beat The Undertaker, he had no career. They later added an additional No Disqualification stipulation to the match.

Under the Arizona-night sky, at the Showcase of the Immortals, The Undertaker and Shawn Michaels did battle once again.

Shawn Michaels focused on The Undertaker’s knees again, in the beginning, when The Undertaker hurt it coming down from Old School. He’d look for any chance to expose the injury throughout the match and torquing his knee with an Ankle Lock. Moving to the outside, Shawn attempted a Springboard Moonsault, but like a year before, The Undertaker caught him and delivered a Tombstone to him on the padded floor.

Neither man was able to hold the advantage for very long, but Michaels had ‘Taker down in the ring and went to connect with an elbow drop, but aware of his surroundings, The Undertaker got his knees up in time to block the elbow. Soon after though, the Heartbreak Kid was able to connect his Superkick, but wasn’t able to capitalize for the win. Making their way back to the outside, Shawn Michaels hit Sweet Chin Music once again, laying out The Undertaker on the announce table. Seeing an open opportunity, he found his way back to the top rope and finally landed a moonsault, placing most of the damage on The Undertaker’s knees.

Ready to end the match and the Streak, Michaels hit his third Superkick, but again, The Undertaker was able to kick out at two. Going to the well one too many times, HBK started tuning up the band, but this time the Phenom side-stepped it and delivered a Chokeslam.

The Undertaker’s second Tombstone wasn’t capable of holding down the Showstopper, but Shawn Michaels body showed he had taken just about all he could take. With Shawn Michaels staggering to his feet, The Undertaker was ready to finish him off, but in a bout of sympathy yelled at Shawn to stay down. In defiance though, Shawn slid his thumb across his throat, mocking The Phenom, daring him to finish the match. When that didn’t work, he slapped The Undertaker across the face, leading to a third and final Tombstone and the win. Making The Undertaker 18-0 and costing Shawn Michaels his illustrious career.

When the match ended, The Undertaker stood up to Shawn Michaels to shake his hand and hug the man whom had given him his greatest Wrestlemania matches of his career.

The Verdict

The Undertaker and Shawn Michaels were meant to be. As I said before, no two men could have performed a better match.

Most will argue that their original Wrestlemania match was the better of the two, which may be true, but I’d argue that the build up was far superior the second time around. As great as the theatrics and storytelling was for Wrestlemania 25, the appeal to the emotions in the build for Wrestlemania 26 surpassed them. Whether the fans knew the final outcome of the match, the vignettes that were aired captured the imagination of everyone who saw them.

For me personally, this build up was perfect. In a time of wrestling when very few performers can suspend the belief of the fans, these two Superstars did it two years straight.

The same reasoning goes for this match as it did for their match at Wrestlemania 25. Shawn Michaels’ time as an in-ring competitor was up and he simply wanted to go out and give a match that could rival all of his other phenomenal matches, which he did.

It wasn’t about winning or losing. It was only ever about two legendary Superstars, one at the end of his career and the other the last of the immortals, going out and doing what no one else can do, on the grandest stage of them all, Wrestlemania.

The Undertaker – 18-0

Who could have ended The Undertaker’s Streak?

After going through The Undertaker’s 18 Wrestlemania matches, I can say that I don’t believe anyone will ever defeat the Streak.

If I had to choose though, I’d say the final list of who had the most potential to end The Undertaker’s Streak is quite short. In my opinion only three Superstars, over the last two decades, come to mind.


As I pointed out in Part 1, The Undertaker’s fifth Wrestlemania opponent, Diesel, could have ended the Streak.

If WWE had wanted Diesel to leave Wrestlemania XII as the winner, there wouldn’t really be any reason to argue against it. However, because Kevin Nash was on his way out of the company not too long after Wrestlemania XII, to head to WCW; I think the decision was made to give the win to The Undertaker because he wasn’t going anywhere.

In the short run, very little have changed. In the long run, The Undertaker’s Streak would be non-existent and perhaps we wouldn’t have had the NWO and the Monday Night Wars, at least not as we know them now.


Upon his debut, Kane had The Undertaker’s number more than anyone before him. He’d shown how his strength, agility and supernatural powers rivaled those of his older, half-brother. Up to that point, even more so than Diesel, it made sense that The Undertaker’s Streak would finally see the end Wrestlemania XIX.

What keeps me from choosing Kane as the one who could have ended the Streak is the story behind their match. If the build up had been changed slightly, in a way that showed The Undertaker didn’t have reservations about facing Kane, but instead fought back to honor his parents and stop Kane and Paul Bearer from continuously defaming their lives.

A stronger, more aggressive Undertaker, starting from the beginning of their feud, would have given much more believability to Kane ending the Streak and would let The Undertaker end the feud as an even stronger face when he was finally able to defeat his brother. Their rivalry would have still been great and Kane may have had a stronger singles career.

Randy Orton

Lastly, the only real potential, Streak-killer, in my opinion, given all the facts and information I have now, is Randy Orton.

The greatest argument can be made for Orton, who at the time of Wrestlemania 21, was showing every characteristic that would make him into the Superstar he is today, but had he won and ended The Undertaker’s Wrestlemania Streak, I’m not sure the skies could have contained his potential.

As a singles competitor he was growing and after his heel turn, becoming the Legend Killer, he could have established himself as the ultimate heel and true Legend Killer with a win over The Undertaker.

He was so young, relevant, exciting and ‘got it,’ enough to know how to work it, had he actually won the match. A young, hot, rookie heel, who had just defeated The Undertaker at Wrestlemania – I imagine the heat he could have gotten would have been something great.

I honestly believe that over some time, after making a face turn, his popularity could have potentially rivaled that of ‘Stone Cold’ Steve Austin and The Rock’s. Instead of John Cena as the face of the company, Randy Orton could have been the face of the WWE.

Some may argue that a still-relatively new Superstar ending the Streak would be a case of ‘too much, too soon,’ which is understandable, but the way I see it is that getting the win over The Undertaker would have given him an immense amount of credibility, more than any title reign could have given him. And that’s what would have really pushed him, if he’s made to look like a legit Superstar, with the help of other established Superstars, the fans are going to believe that he is a real Superstar.

Knowing what I know now about Randy Orton and his in-ring capabilities and how he’s developed his character over the years, the monumental push that he would have received would have no doubt sent him to the top of the WWE sooner than he had, but more importantly, I think he, more so than any other young Superstar at the time, would have been capable of running longer and faster with that ball and making the most of it.

The level he is at now, he would have reached a lot sooner, putting him in that ‘sweet spot’ for a longer time, giving him more opportunity to extend the same favors to other young Superstars of today.

If any one Superstar had to break The Undertaker’s Wrestlemania Streak, I don’t believe that anyone could have done more with that honor than Randy Orton.


Thank you to all those who’ve read through this entire series. As I’ve said before, this is all my opinion based on my knowledge now. If there are any discrepencies, I’d appreciate the feedback.

Most importantly, I’d love to hear what you have to say about my opinions and what your opinions are on this subject – tell me who could have ended The Undertaker’s undefeated Wrestlemania Streak?

Wrestlemania XXVII Prediction

The Undertaker – 19-0


3 thoughts on “Who could have ended The Undertaker’s Streak? – Part 4

  1. I agree—the streak will not die. It’ll always be Taker’s legacy – his Hall of Fame moment. I disagree about Diesel possibly being ‘the one.’ I remember around the time of WM 23 how much hype Batista was getting and what a hard on PS Hayes had for Dave that I was sure Batista was going to win. I’m glad he didn’t – but I thought they were going to have him go over.

    • To Batista’s credit, he worked that entire feud to his advantage. Even with losing at Wrestlemania, I think he came out looking great.

  2. Pingback: Who could have ended The Undertaker’s streak? Part 3 « Lucha Lucy's Wrestling Blog

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