The Greatest Wrestling Match of All Time - SHAWN MICHAELS vs. UNDERTAKER
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Published on August 29th, 2016 | by Pro Wrestling Stories

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The Greatest Match of All Time

SHAWN MICHAELS vs. UNDERTAKER – “One To Go Out On”

Authors: Joey FinneganJ Zarka

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


“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.”

-SHAWN MICHAELS


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Wrestlemania XXV [Photo courtesy of WWE.com]

WrestleMania XXV took place 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. One match, however, stole the show.

More than that, this match is widely regarded as one of the best matches in WrestleMania history. If not, the best match of all time.

It’s a true classic so good that even everyone’s favorite curmudgeon, Bret Harthad 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.

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 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.


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