The last time these men feuded
Although it didn't last long, one of the greatest feuds in WWE history was between these two men back in 1997 and 1998. The troubles between them started when Shawn accidentally cost the Undertaker the WWE Championship at SummerSlam '97 when he accidentally hit the Undertaker with a chair that was meant for Bret Hart. Their match at In Your House: Ground Zero ended in a no-contest. In order to make sure that their next match ended conclusively, the WWE created the Hell in a Cell match.
That match is one of the best matches the WWE put on in the '90s. Not only did this match put the popular Hell in a Cell Match on the map, it also featured the debut of Kane, and Shawn Michael's win led him to fight Bret Hart at the Survivor Series in what has been referred to as "The Montreal Screwjob".
The final match of this trilogy doesn't lack for history either. In a casket match at Royal Rumble '98, Shawn Michaels won the battle but lost the war. During the match, his back hit into the casket in such a way that he suffered an injury that would lead to him being unable to wrestle for over four years.
How will losses impact their future at WrestleMania
If Undertaker loses, the streak will be over. With that, so will a huge part of his mystique and a huge selling point of future WrestleMania events. A loss by Shawn will mean nothing. While he puts on great matches at this event, he only has a 6-9 record at the show. His WrestleMania legacy is built on having great matches, not outcomes that are in his favor. The readers of Pro Wrestling Illustrated have named his losing matches at 5 different WrestleMania events as the match of the year. For those curious, the five losses were to Razor Ramon, Diesel, the triple-threat match against Triple H and Chris Benoit, Kurt Angle, and John Cena.
And the winner will be...
The Undertaker. A loss at WrestleMania will have no impact to the career of Shawn Michaels. However, a loss by the Undertaker here can hurt the wallet of Vince McMahon. There is still a huge potential match for an undefeated Undertaker to place his streak on the line in. A battle between an undefeated Undertaker and John Cena at WrestleMania has the potential to set some box office and PPV records for the WWE.
Photo of the Undertaker is © 2009 World Wrestling Entertainment, Inc. All Rights Reserved. The Undertaker can be seen every Friday Night on the MyNetwork TV program Friday Nigh SmackDown.