#1 The Undertaker vs. Shawn Michaels – WrestleMania XXVI – Streak vs. Career

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The Undertaker and Shawn Michaels had an epic encounter in 2009, so naturally, they had to do it again. But things were different this time, with this match having much higher stakes. Not only was Shawn desperately trying to beat the Streak, but his career would end if he lost. That made this match so much more dramatic, as every pinfall and submission risked ending Shawn’s career.
While their first WrestleMania encounter saw both men on equal footing, this match was all about Michaels’ unyielding determination. It felt much more like Michaels was trying to win no matter what and was fighting with the odds stacked against him.
Michaels fought from below in this match, and resorted to more high-risk moves, like his Moonsault off the top rope onto the Spanish announce table. In one of the most dramatic pieces of storytelling ever seen in WWE, Undertaker looked down in pity at Shawn, only for HBK to slap ‘Taker in defiance. This, in turn, led to ‘Taker hitting the spike/leaping Tombstone, putting an end to Shawn’s storybook career (at least, until WWE Crown Jewel, which effectively nullified the drama and significance of this match).
Just like in 2009, this match was voted Match of the Year by the Wrestling Observer Newsletter. In putting on this set of legendary matches, Undertaker and HBK managed to do what only one other duo could: win the Match of the Year award twice in a row.