The Undertaker's 24 WrestleMania Matches Ranked - From Worst To Best

7. Vs. Triple H - WrestleMania XXVII

Taker Mania XXX
WWE.com

The second Triple H Vs. Undertaker match was something very unique to WWE, and it perhaps isn’t given enough credit for that.

The portrayal of the Undertaker character was daring. Just one year earlier, he had retired Shawn Michaels in what had become a typically sensational ‘Mania performance, but after a liberally and literally destructive and breathless opening two thirds, Triple H assumed the advantage with three Pedigrees. 'Taker kicked out. The rule of three finishing moves had been broken; Triple H had to reintroduce the steel chair to break the Undertaker. He smashed it across his back countless times, each resounding thud more sickening than the last.

The plight of the Undertaker went far beyond sympathy. As he lay there, stricken, he had become pitiable. Triple H, with conflicted body language, implored his opponent to “stay down.” He then drilled ‘Taker in the face. Another rule had been broken. In order to cast doubt over the outcome, Triple H and the Undertaker had to operate beyond the confines of what a WWE match could look like.

In the end, ‘Taker won with an opportunistic Hell’s Gate, but it was a pyrrhic victory. He could not leave the stadium under his own power.

The epic war reinforced Trips’ Cerebral Assassin character and added much-needed shade to the Dead Man. He had never looked as human as he did here.

Contributor
Contributor

Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!