Undertaker Says Sting Dream Match Was WrestleMania’s Biggest Miss

The Undertaker still can’t explain why WWE never pulled the trigger on a match with Sting, and on the latest episode of his podcast, Six Feet Under, he made clear the frustration hasn’t faded with time.

Undertaker said the pairing felt like an obvious main event given how loudly fans had clamored for it, but Vince McMahon simply never bought in. “Obviously the people had already been clamoring for that match for a long time, and it seems like a no-brainer,” Undertaker said. “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.”

What stands out most is that Undertaker says he never actually got a straight answer from McMahon on why the match was passed over. He noted the two never had an in-depth conversation about it, leaving him to guess at the reasoning to this day. “I don’t really have an answer,” he said. “That one just seems like a home run that was just, you know, they decided to walk the guy instead of pitch to him. I don’t know what happened there.”

Despite the lingering mystery, Undertaker was firm that he holds no personal regret, since the call was never his to make. “It wasn’t my decision, but my goodness, I would have loved to have been able to have that match,” he said. He also recalled a brief, almost surreal exchange with Sting after the WrestleMania where fans expected the dream match to finally happen, when the two found themselves on the same flight. “I remember us being on the same plane together, talking. I don’t know why. This is beyond me.”

Undertaker predicted the what-if will never stop being a topic of conversation among wrestling fans, calling it the single biggest missed opportunity in WrestleMania history. “It’ll be discussed for the rest of time,” he said. “I think Sting, that’s probably got to be the biggest miss of a WrestleMania. Those two characters would do some incredible business.”

The backstory only adds to the sense of a lost chapter. Sting didn’t arrive in WWE until 2014, well past his and Undertaker’s primes, wrestling Triple H at WrestleMania 31 before a program with Seth Rollins was cut short by a neck injury. He resurfaced in AEW in 2020 and closed out his in-ring career there in 2024, meaning the two icons — who spent decades as the standard-bearers of WCW and WWE, respectively — never crossed paths in a ring under either banner.

For a generation of fans who grew up imagining Undertaker versus Sting as the ultimate crossover dream match, hearing The Deadman himself admit he’s just as puzzled as everyone else only deepens the mystique. With both men now retired from full-time competition, this is a WrestleMania moment that will live on purely in speculation — one more entry in wrestling’s long list of “what could have been.”