The Undertaker still doesn’t know why he never wrestled Sting — and he believes it remains the biggest missed opportunity in WrestleMania history. Speaking on the latest episode of Six Feet Under, he said the match seemed obvious to everyone except the one person whose opinion mattered most: Vince McMahon.
Undertaker explained that fans had been clamoring for the match for years and that he personally viewed it as a guaranteed main‑event attraction.
“Obviously the people had already been clamoring 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, and I was like, man, this is a home run. This is an easy main event for a pay-per-view.”
He said he never received a real explanation because he never pushed for one.
“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 versus Undertaker… that one just seems like a home run that was just, you know, they decided to walk the guy instead of pitch to him.”
Undertaker says he has no regrets — but wonders what could have been
Undertaker made it clear the decision wasn’t his and that he doesn’t carry any regret, even though he would have loved the match.
“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… I guess it just wasn’t meant to be, but what could have been?”
He recalled one brief conversation with Sting after a WrestleMania where the match didn’t happen.
“I remember running into Sting… I remember us being on the same plane together, talking. Like, I don’t know. This is beyond me. I don’t know. I don’t know why.”
“The biggest miss of a WrestleMania”
Undertaker believes the question will outlive both men.
“It’ll be discussed for the rest of time. A what if… I think Sting, that’s probably got to be the biggest miss of a WrestleMania. Those two characters would do some incredible business. I just, I don’t, sorry, I don’t know. Wasn’t me. Wasn’t me.”
Sting signed with WWE in 2014 and wrestled only twice — against Triple H at WrestleMania 31 and Seth Rollins at Night of Champions — before a neck injury ended his run. He later returned to full‑time competition in AEW in 2020 and retired in 2024.
The dream match remains one of wrestling’s most enduring “what if” scenarios, and according to The Undertaker, it always will.
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