The Undertaker's 23 WrestleMania Matches - From Worst To Best

9. Randy Orton (WrestleMania 21)

Randy Orton's "Legend Killer" character had taken WWE by storm in 2003 and, after an ill-fated and short-lived stint as a babyface, he returned to the dark side just in time to face The Undertaker at WrestleMania 21. Fitting, huh? The brash Orton was confident in his abilities to end the legend's undefeated streak, but he found out the hard way just how difficult a task that was to accomplish. Even with the assistance of his father, Hall of Famer "Cowboy" Bob, interfering. Late in the match, he even managed to counter a chokeslam attempt into the RKO, which only managed to put The Phenom down for a two count. His moveset exhausted, Orton's arrogance took over. He attempted to use his opponent's own Tombstone against him, even going as far as to mock the throat-slicing gesture that precedes it. Undertaker reversed, planted his cocky rival and finished him three seconds later, adding Orton to his ever-growing WrestleMania graveyard. The match was more dramatic than the majority of his 'Mania outings to that point. Orton was young, the company's hand-picked choice to lead WWE into the future and if there was anyone that would have benefited exponentially from ending the streak, it would have been him. It really added to the drama of the match. But it was not to be. The counters and reversals on display were a new element of Undertaker's game that he would introduce to all of his matches thereafter, and the result would be beneficial, as evidenced in seven of the next eight matches.