The Undertaker recently addressed why he never faced Sting in WWE, despite their legendary status and fans’ anticipation. During an episode of the Six Feet Under podcast, The Undertaker revealed that he is frequently asked about this potential dream match. He explained that Vince McMahon was not interested in making the match happen.
He revealed, “Everywhere I go on any given day I get the question. I always call it the question. Like when I do the 1 deadMAN Show. I just wait and I’m like, when’s it coming? Because I know it’s gonna come. It’s always, Why didn’t you and Sting ever have a match? Or why didn’t this happen or that happen? Man, that would have been huge box office, it just didn’t work out.”
He continued, “He had a short run in WWE and Vince didn’t want it for whatever reason, I don’t know what it was. He just didn’t feel it. And everybody else was like, people have clamouring for this match for quite a few years. And I mean, I don’t know, a year or two into his turn or that character change, people were sending me artwork with the billboard of the poster. So, yeah, it just never worked out.”
Despite the missed opportunity for what could have been an iconic encounter between two wrestling legends, The Undertaker and Sting never crossed paths in the ring during their respective WWE careers due to McMahon’s decision.
Why The Undertaker feared a match with Sting would be disappointing The Undertaker’s skepticism about a potential match with Sting stemmed from various factors, including timing, expectations, and his own assessment of his abilities at that stage of his career.
Both The Undertaker and Sting were widely respected for their dedication to their craft, their in-ring talents, and their enduring careers. Many fans had fantasized about witnessing a showdown between them. Even though both wrestlers were in WWE together from 2014 to 2016, they didn’t end up having the match. Sting only wrestled a few times in WWE before he retired.
In the same episode of the podcast, The Undertaker revealed his reservations about the match. He expressed concern that the actual match might not have lived up to the lofty expectations fans had built up over the years. He mentioned that people often imagined a match between The Undertaker from 2007 or 2008 against Sting, but by the time they were both in WWE, it was later on in their careers.
The Undertaker acknowledged that he was “way on the backside” of his in-ring career when Sting arrived in WWE.
