For years, wrestling fans have debated why a dream showdown between The Undertaker and Sting never became a reality, and according to The Deadman himself, he is still searching for the same answer.

Speaking on the latest episode of Six Feet Under, The Undertaker admitted he believed the bout was an obvious blockbuster, but said the idea never appealed to Vince McMahon despite overwhelming fan demand.

"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."

While many have speculated over the years about why the match never materialised, Undertaker revealed he never received a clear explanation because the subject was never discussed in depth.

"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. Again, he obviously knows more about business than I do, but 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. I don’t know what happened there."

Although disappointed that the opportunity slipped away, Undertaker stressed he has no regrets, noting the decision was never his to make.

"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, but what could have been?"

The pair even briefly spoke about the missed opportunity after the WrestleMania where many expected it to happen.

"I remember running into Sting. I think it was after the WrestleMania that we didn’t work. 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."

Undertaker believes the unanswered question will continue to fuel discussion among wrestling fans for generations and considers it one of WrestleMania's greatest missed opportunities.

"It’ll be discussed for the rest of time. A what if. What if these two guys would have been able to do it? 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 eventually arrived in WWE in 2014, where he wrestled Triple H at WrestleMania 31 before facing Seth Rollins at Night of Champions. A neck injury brought his WWE run to an early end. He later returned to the ring with AEW in 2020 and officially retired from in ring competition in 2024, leaving the long anticipated clash with The Undertaker as one of wrestling's greatest "what if" scenarios.