Why Sting Vs. The Undertaker Never Happened In WWE

Dream matches often end up taking place in professional wrestling, with just a couple of high-profile matches to actually take place being The Rock vs. Hulk Hogan and Kenny Omega vs. Bryan Danielson, but arguably the ultimate dream match that never happened is Sting vs. The Undertaker.

Both wrestlers were stars in their respective companies during the Monday Night Wars, with Sting in WCW and The Undertaker in WWE, but Sting ultimately opted not to sign with WWE after the dissolution of WCW, instead wrestling for TNA on a full-time basis from January 2006 until January 2014.

From November 2014 to September 2015, though, both Sting and The Undertaker were active wrestlers in WWE, but the dream match that fans had wanted for decades still didn't happen, something that left The Undertaker baffled.

"People had already been clamouring for that match for a long time and it seems like a no-brainer. Like why on Earth would you not do that? But, for whatever reason, Vince did not see it. Didn't like it, didn't want it. I was like, 'Man, this is a home run. This is an easy main event for a pay-per-vew.' But I don’t really have an answer. I never really had an in-depth conversation with Vince about why he didn’t want to do it. My goodness, a Sting vs. Undertaker. Again, he obviously knows more about business than I do, but that one just seemed like a home run. They decided to walk the guy instead of pitch to him. I don't know. I don't know what happened there. I don't have any regrets. It wasn't my decision, but my goodness, I would have loved to have been able to have that match and I guess it just wasn't meant to be. What could have been," The Undertaker said on Six Feet Under.

"I remember running into Sting, I think it was after the WrestleMania we didn't work. I remember we were on the same plane together talking. I was like, 'I don't know. This is beyond me. I don't know why.' It is what it is, man, I guess. I think Sting has probably got to be the biggest miss of a WrestleMania. Those two characters, that would have done some incredible business."

Both Sting and The Undertaker performed at WrestleMania 31, with Sting losing to Triple H in a match set up to be one final WWE victory over WCW 14 years on from the end of the Monday Night Wars. This included WWE commentators being directed to bury Sting during the WrestleMania 31 match. The Undertaker, meanwhile, defeated Bray Wyatt at the pay-per-view.

Dave Meltzer noted on the December 19, 2025 episode of Wrestling Observer Radio that Sting vs. The Undertaker never happened in WWE because Vince McMahon simply didn't see Sting as being on Undertaker's level and the then-WWE CEO didn't think fans would care about the match.

"That's a Vince call and, in hindsight, I guess the answer is no. He never saw the big thing in it that a lot of people did. He could have done it. Many people would have wanted him to do it. I don't think he saw Sting at the level of Undertaker, and he didn't do it. I think if somebody else was in charge, there would have been a pretty decent shot of it. Vince didn't know Sting. His thought on the Sting-Undertaker thing was, yeah, it's a dream match to some people but not to our audience. And he was wrong, but I don't think there was a good chance, no," Meltzer said.

Sting would wrestle two more times for WWE after WrestleMania 31 until he suffered what was, at the time, a career-ending injury in a match with Seth Rollins at Night of Champions 2015. Sting remained under contract with WWE until 2020, when he left the company and signed with All Elite Wrestling. The Icon would come out of retirement and have a critically acclaimed run in AEW that ended on a high note at Revolution 2024.

The Undertaker continued to wrestle for WWE until 2020's WrestleMania 36 in his pursuit of one final great match after he was unhappy with his performance in Undertaker's original retirement match against Roman Reigns at WrestleMania 33. That final match would ultimately be a Boneyard Match with AJ Styles in one final WrestleMania main event.

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