The Undertaker Reveals Which Match He Considers the Greatest of His Career

The Undertaker has competed in hundreds of matches over his storied WWE career, but when asked to choose the one that stands above them all, he didn’t hesitate.

During a sit-down with Tom Segura on 2 Bears, 1 Cave, the wrestling icon finally named what he considers the greatest match of his life—and it’s the unforgettable clash against Shawn Michaels at WrestleMania 25.

After decades of facing legends like Kane, Triple H, The Rock, and Stone Cold, The Undertaker singled out his 2009 showdown with HBK in Houston as the pinnacle of storytelling and performance.

“So the match I’m probably… man, as far as a wrestling purist kind of match, would have to be WrestleMania 25. Shawn Michaels.”
“That was as close to perfect that I ever got.”

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He explained that both he and Michaels were in their 40s at the time, well into the back half of their careers, which only made their performance more powerful.

“We were both in our 40s, both late in our careers. But the story we were able to tell? That’s what wrestling is all about. Wrestling is a soap opera with violence.”

The match wasn’t just physically intense—it played with the emotions of the audience. Fans were fully invested, unsure if The Undertaker’s legendary undefeated WrestleMania streak would finally be broken.

“They all thought there was a chance I was going to lose the streak. That’s the goal—you want them to go through that emotional ride.”

The bout launched a four-year WrestleMania storyline arc, with a rematch at WrestleMania 26 (which served as Shawn Michaels’ retirement match), followed by two brutal battles with Triple H. But for The Undertaker, nothing ever quite matched the electricity of that first WrestleMania clash with HBK. After three decades in the business, that was the one.

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