The 25th Anniversary of WrestleMania was headlined by a title match and stacked with a Money in the Bank ladder war — but it's the "Streak" match between two legends that history remembers most.
WrestleMania 25 took place on April 5, 2009, at Reliant Stadium in Houston, Texas, drawing an announced crowd of 72,744 and generating roughly 960,000 pay-per-view buys. The card's official main event saw Triple H retain the WWE Championship over Randy Orton, and its top-billed title fight was a Triple Threat match in which John Cena dethroned Edge for the World Heavyweight Championship. Neither is what people talk about when they bring up WrestleMania 25.
That distinction belongs to The Undertaker's clash with Shawn Michaels — a match that critics, wrestlers, and WWE itself have spent over 15 years calling one of the greatest of all time. Here are three reasons why it still holds that reputation.
1. The Story Was Told Before the Bell Even Rang
WWE built the match around a simple, powerful visual contrast: light versus dark. Michaels made his entrance descending from above on a platform to symbolize the light, while The Undertaker entered second, rising up from the stage floor as fire shot into the air. It wasn't just spectacle — it set the emotional frame for the entire match before either man threw a punch.
The stakes were built cleanly on WWE programming beforehand, too. Michaels earned his spot by defeating JBL and then Vladimir Kozlov in back-to-back weeks on Raw, while The Undertaker entered as the man protecting his undefeated WrestleMania streak, then sitting at 16–0. That framing — an aging icon trying to end a legend's immortality — gave the match a stake that didn't need extra hype.
2. The In-Ring Work Is Still Held Up as a Model of Match Psychology
The match opened at a fast pace before Michaels feigned a knee injury to slow things down and seize control, kicking off a long exchange of signature moves and submission holds. Michaels escaped The Undertaker's Hell's Gate submission and dodged multiple chokeslam attempts, while The Undertaker blocked repeated tries at Michaels' Sweet Chin Music finisher. When the action spilled outside, an intended stunt spot involving a cameraman went wrong and The Undertaker landed hard on the floor, only to beat a referee's ten-count and continue.
From there, both men kicked out of finisher after finisher — The Undertaker's Last Ride, a chokeslam, and a Tombstone Piledriver all produced near-falls, as did two Sweet Chin Music superkicks from Michaels. The match finally ended when The Undertaker caught Michaels mid-air during a moonsault attempt and converted it directly into a second Tombstone Piledriver for the pin. Longtime broadcaster Jim Ross later said he had never witnessed a more psychologically compelling match than this one, and WWE veteran Arn Anderson has said it's the match he'd show someone who had never seen wrestling before, to guarantee they'd come away impressed.
3. It Won Nearly Every "Match of the Year" Award There Was — And the Wrestlers Meant Every Word
The bout earned the 2009 Match of the Year award from both Pro Wrestling Illustrated and the Wrestling Observer Newsletter, plus Match of the Year honors at the 2009 WWE Slammy Awards. Dave Meltzer of the Wrestling Observer rated it 4.75 stars out of 5, saying it was held back only by a slight predictability in how the finishers were traded — still an extraordinarily high score by his own standards. WWE has since ranked it #1 on its own list of "The 100 best matches to see before you die" and atop its YouTube ranking of the "50 Greatest WrestleMania matches ever."
The praise wasn't just critical — it was personal. Shawn Michaels has called it "the most perfect, beautiful thing I've ever performed inside a wrestling ring" in his career, and The Undertaker has said the two "delivered on every aspect of storytelling and match quality." Bret Hart, no stranger to great WrestleMania matches himself, called it "one of the best matches I've seen in years," while Triple H has separately described it as the greatest match of all time.
WrestleMania 25 will always be remembered as "The 25th Anniversary of WrestleMania" on paper, but in wrestling history, it's remembered as the night Shawn Michaels and The Undertaker put on a match so complete — in build, execution, and payoff — that WWE itself still hasn't ranked anything above it.
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