10 Ways To Successfully Challenge The Undertaker At WrestleMania

4. Cost Him The Title (Shawn Michaels - WrestleMania XXVI)

Shawn Michaels had been so eager to prove himself at WrestleMania XXV that his on-screen character took a hammer blow by failing to beat Undertaker. Known as 'Mr. WrestleMania', Michaels vowed to convince his foe to step foot inside the ring one more time with him, aiming for 'Mania XXVI as the best occasion on which to take another shot at the streak. Initially turning down the advances, 'Taker was brilliantly booked to drop the World Heavyweight Championship to Chris Jericho at the Elimination Chamber Pay-Per-View just over a month before WrestleMania. Chris Jericho capitalised on a HBK Sweet Chin Music, one which cost The Undertaker the gold, and pinned his opponent to bag the belt. Following that, both men now had motivation to meet at 'Mania once more, and it's fair to say they didn't need the title to make the match special. In fact, it was a different stipulation which added fuel to the proverbial fire, as Shawn Michaels entire career was put on the line. What transpired was one of the greatest WrestleMania bouts of all time, and the end of a legendary career.