The Complete A-Z Of The Undertaker
8. S - Shawn Michaels
It's one thing to contest one of the greatest rivalries in the history of the industry. It's another to have one of the all-time great matches as part of the feud. It's fantastic to do both. It's almost impossible to do it twice.
The 1997-98 and 2009-2010 conflicts between 'The Deadman' and 'The Heartbreak Kid' are wars for the ages.
Triggering Michaels' heel turn in late-1997 after a thunderous chair shot from guest referee Shawn cost Undertaker the WWE Title at Summerslam that year, the two engaged in a brutal and bloody war of attrition. Undertaker tried and failed to rip the future DX leader limb from limb in their first contest, but just about succeeded in the historic first ever Hell in a Cell match at October's Badd Blood.
Over ten years later, a confident Michaels thought he could break the WrestleMania streak. Two failures lead to ultimately to his retirement, though not before the pair contested two of the greatest matches ever held at the 'Showcase of the Immortals'.