The Best WrestleMania Matches of All Time: The Undertaker vs. Shawn Michaels


No wrestler is as closely tied to WrestleMania as the Undertaker. Headlining WWE’s hallmark pay-per-view on more than one occasion, the Undertaker has been featured in some of wrestling’s all-time classic matches showcased on the “grandest stage of them all.”

Making his first WrestleMania appearance at WrestleMania VII in 1991, the Undertaker became one of the PPV’s foremost attractions, thanks mainly to his legendary undefeated streak that lasted just over 20 years.

Known simply as “the Streak,” challengers far and wide tried hard to score a win over the Dead Man, only to be met by inevitable failure time and time again. Even when the Undertaker’s Streak finally came to a close (courtesy of Brock Lesnar in 2014), the Undertaker still had an array of rich matches forever attached to his name.

When looking at the spectrum of the Streak, it’s clear that some of the Phenom’s WrestleMania matches were far better than others. From his matches against fellow legends like Shawn Michaels and Triple H to rising stars like Randy Orton, Batista, and CM Punk, here are some of the greatest WrestleMania matches to feature the Undertaker.

1. The Undertaker vs. Shawn Michaels (WrestleMania XXV)
Shawn Michaels’ bout with the Undertaker at WrestleMania XXV not only has the distinction of being either man’s best WrestleMania match-up — it’s also one of the single greatest professional wrestling matches of all time.

Beating Vladimir Kozlov and earning a right to challenge the Phenom at WrestleMania, Michaels looked to make history, putting his born-again Christian values against the demonic presence of the Undertaker. Surpassing storylines alone, the match also reignited the excellent 1997 feud between Taker and Michaels and their epic standoffs at the 2007 and 2008 Royal Rumble events.


In retrospect, no two athletes were as iconic as the Heartbreak Kid and the Demon of Death Valley, both men serving as staples of WWE programming throughout the Attitude Era and Ruthless Aggression Era. So naturally, there was a lot of hype surrounding the bout, but both men surpassed expectations, delivering the finest match in WrestleMania history.

2. The Undertaker vs. Shawn Michaels (WrestleMania XXVI)
In the 2010 rematch between Michaels and the Undertaker, what set WrestleMania XXVI apart from its predecessor was the utterly fantastic storyline moving into the match. Sensing that he had come exceptionally close to beating the Dead Man and breaking the Streak, Michaels slowly became obsessed with challenging the Undertaker to a rematch — a challenge Taker promptly refused, claiming a second bout would only lead to more disappointment for HBK.

Consumed by his growing need to break the Streak, Michaels spent the early portion of 2010 pining after the Undertaker, coming close to winning the 2010 Royal Rumble match (earning a title match against Taker) and costing Taker the World Heavyweight title at the Elimination Chamber pay-per-view. Infuriated, the Undertaker finally accepted Michaels’ challenge, with the added caveat that, should Michaels lose, he would be forced to retire (echoing the stipulation in Michaels’ match against Ric Flair at WrestleMania XXIV).

While their initial 2009 match was only marginally better, the storytelling behind the bout was fantastic. As with all the best wrestling matches, each man told a story in the ring, fueled by Michaels’ desperation to retain his career and the Undertaker’s desire to protect his Streak.


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