Ranking Triple H's 19 WrestleMania Matches - From Worst To Best

5. Triple H Vs. The Undertaker (WrestleMania XXVII)

The WrestleMania XXVII battle between Triple H and The Undertaker had no convoluted backstory, nor did it need the reemergence of the McMahon family to help lend it heat. It was simplistic in nature, an undefeated force of nature battling an all-time great who was certain he could do what no other man had to that point and defeat The Phenom. With 71,000 fans watching in Atlanta, and another million fans viewing via pay-per-view, The Game would come closer to defeating Undertaker at WrestleMania than any other Superstar ever had. Triple H delivered three consecutive Pedigrees to Undertaker, this after surviving a Tombstone piledriver, but could not put his opponent away. Frustration and arrogance getting the best of him, he even used The Deadman's Tombstone against him. No matter what, though, nothing would put away Undertaker or his undefeated Streak. Eventually, Hunter found himself trapped in the clutches of his opponent, stuck in the Hell's Gate submission that would prove his demise. The match takes a great deal of suspension of disbelief to appreciate. Is it at all possible, even in the make believe world of professional wrestling, that Undertaker would have kicked out of three of his opponent's finishers, not to mention one of his own? Of course not. But that bit of booking was necessary to get to the endpoint desired, which was a beaten, battered, bruised Undertaker winning but needing to be carried out on a stretcher. Triple H, the actual loser, had taken his opponent to a level never before experienced by the Deadman and the result was the near demolition of his undefeated streak. It set the stage for a five star classic the following year, but more on that in a moment.