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.
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.
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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