#2. The Phenom defeated Mr. WrestleMania - WrestleMania XXVI, 2010
Shawn Michaels was perhaps more desperate than anyone else to break the streak. Having failed to do so at WrestleMania 25, he tried everything to convince the Undertaker for a rematch.
The Deadman accepted the challenge at the stipulation that Michaels would have to retire if he lost. The Heartbreak Kid agreed to earn his rematch.
Their match at WrestleMania 26 was spectacular. It was probably the only instance where fans were equally supporting the Last Oulaw's opponent at WrestleMania because his career was on the line.
Eventually, The Phenom ended Michaels' career in what was a thrilling contest right from the beginning.
#1. The Undertaker defeated Shawn Michaels - WrestleMania XXV, 2009
The first match between Shawn Michaels and Taker at WrestleMania was certainly the better of the two bouts. Their match was booked when Michaels claimed himself to be capable of ending the streak.
Not only was it the best match of Undertaker's or Michaels' career, but it was also arguably the best in WrestleMania history. It's hard to believe that the two superstars were above 40 in the match, putting on a thrilling encounter.
Ultimately, Taker bettered his score from 15-0 to 16-0.