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The Undertaker has faced almost every legend in WWE over the course of his 29-year career, with one of his standout opponents during that time being Shawn Michaels.
Between 1990 and 1997, the two men often competed with and against each other in dark matches and at live events, but they did not meet in a singles match on WWE television until In Your House: Ground Zero in September 1997.
It was revealed by Michaels in the latest episode of ‘WWE Untold’ that Vince McMahon rejected the idea of him facing The Undertaker on multiple occasions and never wanted them to go one-on-one.
“Prior to this storyline between The Undertaker and Shawn Michaels, there had been times over the years when people within the WWE had presented, ‘How about Shawn Michaels, the Heartbreak Kid, against The Undertaker?’ and, of course, at the time, Vince McMahon was very emphatic about, ‘Those two will never be in the ring with each other’.”
WWE Producer Bruce Prichard, a key member of the creative team in the 1990s, added that it would have been difficult for either Superstar to emerge from the rivalry with their reputation enhanced, which is why McMahon did not want them to feud with each other.
“You have these two strong personalities, Shawn Michaels and The Undertaker, that when they collide… what is the finality of that? Because you have to keep both guys whole, you have to keep both of those attractions strong.”
The Undertaker and Shawn Michaels’ legendary rivalry
One month after their first meeting at In Your House: Ground Zero, Shawn Michaels defeated The Undertaker in the first Hell In A Cell match in WWE history at In Your House: Badd Blood following interference from the debuting Kane.
Over a decade later, this rivalry was cemented as one of the greatest of all time when “The Deadman” defeated HBK at back-to-back WrestleManias in 2009 and 2010, forcing him to retire.
In 2018, Michaels came out of retirement when he teamed with Triple H to defeat The Undertaker and Kane at Crown Jewel, ending the rivalry once and for all.
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