The Greatest Match of all Time: The Story Behind The Undertaker and Shawn Michaels

“What is the greatest match of all time?” Many fans have been debating this question for years. One answer that is always part of the equation is a match that took place at WrestleMania 25 on April 5th, 2009, at the Reliant Stadium in Houston, Texas, the respective home state to both the ‘Heart Break Kid’ Shawn Michaels and The Undertaker. It boasted an attendance of 72,744, as well as 960,000 pay-per-view buys, totaling somewhere around $21.0 million in revenue. Critical reception was mixed.

This match stole the show and is widely regarded as one of the best matches in WrestleMania history. If not, the greatest match of all time.

The Undertaker and Shawn Michaels square off at WrestleMania XXV in what many consider the greatest match of all time.
The Undertaker and Shawn Michaels square off at WrestleMania XXV in what many consider the greatest match of all time. [Photo courtesy of]

“We’re two guys that a lot of folks see as warriors who can do everything under the sun, and we can pull one another aside and know otherwise. We can do our best, but all you can do in a situation like that is give each other a squeeze and let each other know we’re moving on, and it’s like everything — we’ll worry about it afterward…

I look back at things and I can be real critical of myself. There aren’t many times I’ve come out of the ring when I haven’t felt like, Oh, you know, I could have done something better…I could have changed this or changed that.

But that match…that’s one that I don’t know I can say that with.”


The stage at WrestleMania 25 with pyrotechnics going off
WrestleMania XXV [Photo courtesy of]
It’s a true classic so good that even everyone’s favorite curmudgeon, Bret Hart, had praise to offer (while of course also slipping in a bit of praise for himself, too):

“I’ll be the first to say that I thought Taker vs. Shawn was the best match at WrestleMania, maybe one of the best matches I’ve seen in years,” Hart told the UK Sun. “To a certain degree, I was proud of both of them. I never take away the fact that Shawn was a great wrestler and he did a lot of great stuff. I’ve always been really proud of the match we had in Anaheim when I dropped the title to him.”

The two competitors were no strangers to one another in the ring. In their sixteen years together in the company, they squared off a total of five times: three times in 1997 but not again until 2009, though they did manage to interact from time-to-time behind-the-scenes.

For a while, Shawn and Undertaker didn’t get along in real life. As the story goes, in 1998, Taker wrapped up his fists ready to deliver due justice to Michaels if he didn’t do the job for Austin at WrestleMania XIV. Taker, like many others, got sick and tired of seeing Shawn mess around with WWF business, especially after what happened a few months before at Survivor Series and what is now infamously known as the Montreal Screwjob. Would Michaels do the right thing and put Austin over or would he pull some shenanigans again? Undertaker as locker room leader was taking no chances. Before the match, he got in Michaels’ face and showed his fists, letting the egotistical star know that if he did anything other than put Austin over he would face the consequences.

Related: The Montreal Screwjob at Survivor Series 1997

Luckily for Shawn, Stone Cold‘s coronation went as planned. Michaels took off for a few years after this match to heal and find himself while the era of Austin officially set off into the stratosphere. Meanwhile, Undertaker unwrapped his wrists and carried on with his business as normal.

Most of us know the story by now of how Shawn Michaels found God and overcame his drug habit. By 2002, he returned to the ring full time. In what was supposed to be only a one-match affair turned into eight more years in the company, which firmly secured his place in the conversation of the greatest in-ring performers of all time. Many were still skeptical over whether or not Michaels had actually turned over a new leaf or if he would relapse back to his past behaviors when he wanted an advantage in the company.

Shawn Michaels had, in fact, become a changed man and he and Undertaker were the reigning elders in the back, leading the locker room as the only two members of the roster who were there on the first episode of Monday Night Raw. Not only that, they were both enjoying the second primes of their career.

In 2007, we got an unexpected glimpse at an absolute gem, Taker, and Shawn squaring off in the ring for the first time in a decade as the last two men in the Royal Rumble. They put on a ten-minute clinic and reminded the world just how great they can be together. This planted the seeds for an extended program between the two legends.

The Greatest Match of All Time: The One Time Vince McMahon Didn’t Cut it Short

before the greatest match of all time Shawn Micheal's making an entrance in all white descending from above
Shawn Michaels makes his glorious entrance at WrestleMania XXV [Photo courtesy of]

The Heartbreak Kid made his entrance first, gloriously so (as you can see in the image above). They went the obvious route for a storyline with this match. Shawn was famously born again, and Taker was – well – Taker, playing the role of Lucifer.

It was good versus evil.

Dark versus light.

Shawn Michaels and Undertaker performed their parts beautifully. By the time the bell rang, all they needed to do was turn in a match on caliber with the ones they’ve had before, and the fans would have been happy.

The undertaker making his entrance in all black on the runway at WrestleMania 25
The dead man cometh [Photo courtesy of]

Other than the titular classic, the 25th Anniversary of WrestleMania wasn’t exactly spectacular. The rest of the card is full of bouts that could’ve taken place on Backlash, or Unforgiven, or any other run of the mill PPV. Shawn and Taker could have put in minimal effort and they would’ve outdone the rest of the roster.

Of course, that was not their style. The Showstopper and The Phenom went above and beyond their call of duty that night, producing some truly magnificent storytelling in the ring in the process.

Most people were expecting a good match. They were veterans who were capable of doing something special. But what we got was something much more. The match actually wasn’t even supposed to be that great. They had gone over their allotted time while only halfway through with what they had planned to do. Usually, in these situations, the match agent or Vince would tell the referee to tell the wrestlers to cut their match short. But this was different. Michael Hayes was the agent for the match and he recently broke down the backstage reaction to the bout going long on Ric Flair’s WOOOO! Nation podcast:

“They were only halfway through and the allotted time…I was looking like ‘they have 10 more minutes [of match time] and at least 25 more minutes to go…And Vince comes over the headset and says, ‘I don’t care. Let ’em go.’ And everyone else had to follow suit.”

The match stole the show and instantly became the blueprint for any big stage match that followed.

Hell, during the match, The Dead Man actually almost became dead, man.

The Greatest Match of All Time almost Took Out the Undertaker…and who won?


SHAWN MICHAELS on The Undertaker’s horrible landing from his suicide dive:

“You hear the gasp of the people… I was pushing one guy* and didn’t actually see the impact, but I remember looking over and seeing the little indentation [in the mat] and obviously being concerned…but he was moving, so I figured that was good.

Unfortunately for The Undertaker, we’re sort of get accustomed to thinking he’s 10-feet tall and bulletproof, and a lot of times that works against the poor guy. I think certainly that’s something that we’re aware of and cognizant of that, even in respect to one another.

We’re two guys that a lot of folks see as warriors who can do everything under the sun, and we can pull one another aside and know otherwise. We can do our best, but all you can do in a situation like that is give each other a squeeze and let each other know we’re moving on, and it’s like everything — we’ll worry about it afterward…”

(*The ‘cameraman’ Michaels pushed was played by Sim Snuka, son of Jimmy and sister to Tamina – a knowing wink back in time to the very first streak match.)

Thankfully, Taker survived the suicide dive and kept on working his ass off. Then, after one of the most physically and emotionally moving wrestling matches in history, Taker managed to catch Shawn and put him away with a final Tombstone Piledriver.

[Quote above compiled by Matt Pender and shared here with thanks to our friends over at Wrestling’s Glory Days’ Facebook page]

I remember going home after [WrestleMania 25] and saying to my wife, ‘That was pretty good…maybe THAT should have been my last…”


As we know, the greatest match of all time was not his last. One more final battle between the Undertaker and Michaels was to come…

The Undertaker hits a jumping tombstone piledriver on Shawn Michaels at WrestleMania 26. This would mark the final moments of Shawn Michaels' illustrious in-ring career.
The Undertaker hits a jumping tombstone piledriver on Shawn Michaels at WrestleMania 26. This would mark the final moments of Shawn Michaels’ illustrious in-ring career. [Photo courtesy of / Uproxx]


Back in 2015, Jim Ross held a special called “Through The Eyes Of Jim Ross: A WrestleMania Retrospective”, via Busted Open Radio on Sirius. Shawn Michaels was a special guest. The following is a transcription of both WWE legends covering their opinions on whether or not HBK vs. Taker at WM XXV truly is the greatest match of all time in the Showcase of the Immortals.

 Shawn Micheals and Jim Ross on Whether the WrestleMania 25 with the Undertaker was The Greatest Match of All Time


“It was a phenomenal match from my standpoint. I don’t know if you can wrestle a perfect match but it certainly felt that way to me. On the ride home, I can remember saying, ‘Well, that might have been the one to end it on. That was pretty darn special.’ So you knew it was good when you were doing it. You knew it was special afterward. I will let history decide where it ranks because again, all that stuff is subjective, and depending on who you ask, all those opinions differ as well. So I try not to get too caught up into it, but it was certainly special to me.”


“I was kind of on the outs and fading away at WrestleMania 25. Probably one of the greatest gifts I’ve ever had was to be able to call that match with Cole and Lawler. And I just thought it was a piece of art. And I’ve seen a lot of matches and I’ve seen Shawn since day-one in the Mid-South territory. I tell kids this all the time when I do my one-man show; they say ‘Well, if I want to watch a match and understand psychology…’ I say I can give you a lot of matches that have great psychology. Because back in the day, there was some amazing in-ring psychology. But if you want to go in modern time and I certainly consider WrestleMania 25 a modern era match, I have never seen a more psychologically compelling match than Shawn and Taker had that night. I had goosebumps. I had tears in my eyes. I was so emotionally wrapped up in that presentation. So if I was, as the grizzled veteran, if I was emotional, I can only imagine the impact it had on younger wrestling fans. I think on our drive home we were on the money, that might have been the one to go out on.”

WrestleMania 26 brought about the final chapter in the Shawn Michaels / Undertaker story through a Career vs. Streak match. If Michaels was victorious, he would break the Undertaker’s unbroken streak. If Undertaker won, Michaels would retire. The match was justly the main event and it was another classic. Even though it wasn’t as good as the one before, it still lived up to the impossible hype and the bar set by WrestleMania 25. In the end, Undertaker won with a jumping Tombstone.

The following night, Michaels gave his retirement speech on RAW. While Shawn addresses the crowd, Undertaker came down to the ring, got on one knee and saluted his once-rival. Over the years since Michaels returned and they revived their in-ring feud, they earned each other’s trust and became real-life friends. They shared one of those bonds that only wrestling can bring.

Watch Undertaker come to the ring to salute Shawn Michaels during his retirement speech on RAW (did somebody cut some onions in here?):

“At the time of that match, and knowing it was going to be my last, I think I might have been able to see some sort of downside in my career.

But now, all these years later, I don’t.

There were ups and downs, sure, but as I look back now, all I see is absolute joy and pleasure. He and I didn’t know we could get any closer after the first match [at WrestleMania 25].

We were wrong.

We could, and we did.

And it’s one of those things I’ll have forever.

To me, nothing compares to putting on a good show. And I mean that with respect to this entire business. But, truthfully, the wins, the losses, the championships — none of those things are as important as putting on a good match.

He and I sat in the same locker room forever. We were just two, battle-worn warriors who had been going at it for a long, long time. And that match was just a great final memory to have. Because of that, the peace of my retirement is only greater now.”


Due to the greatest match of all time and the masterful work they put out at back to back WrestleMania’s, HBK versus Undertaker will be forever known as a legendary rivalry in the annals of WWE history and as of now truly goes down as the greatest match of all time.

Purchase this Wrestlers' Court shirt featuring Undertaker, Yokozuna, and JBL on today!
Purchase this Wrestlers’ Court shirt featuring Undertaker on today!

SOURCES for The Greatest Match of all Time: Baltimore Sun, WWE, Shawn Michaels: ‘My Journey’Wrestling’s Glory Days’ Facebook page, Uproxx, WOOOO! Nation podcast, wrestlinginc

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