The Undertaker believes Vince McMahon passed on the biggest dream match WrestleMania never delivered. On Six Feet Under, he named a bout with Sting as a home run WWE should have booked and put the blame on McMahon for it never happening.
Fans had called for The Undertaker versus Sting for years, and the subject returned on the podcast when talk turned to Sting’s 2014 arrival in WWE.
“Obviously, people had already been clamoring for that match for a long time, and it seems like a no-brainer,” Undertaker said. “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.”
A one-on-one conversation with McMahon about the call never took place. Undertaker said he holds no regrets over it, while making clear he would have loved the match.
One WrestleMania miss stood out above all others in his mind.
“I think Sting, that’s probably got to be the biggest miss of a WrestleMania. Those two characters, that would have done some incredible business,” Undertaker said.
Undertaker holds a WrestleMania record of 25-2, the finest mark at the event in WWE history. The famous undefeated streak reached 21-0 before Brock Lesnar ended it at WrestleMania 30 in 2014.
A win over Bray Wyatt followed at WrestleMania 31 in 2015 at Levi’s Stadium. The Levi’s Stadium card was the stage many fans had pictured for Undertaker and Sting, and the dream pairing never appeared on it.
Undertaker wrestled his final match at Survivor Series in 2020 and entered the WWE Hall of Fame in 2022. The list of his marquee WrestleMania opponents runs long, including Shawn Michaels, Triple H, Edge, and Shane McMahon.
Sting spent the prime of his career as the franchise of WCW and never set foot in a WWE ring during the Monday Night Wars, which is why a match with Undertaker lived so long as a fantasy. Sting’s arrival at Survivor Series in 2014 saw him confront Triple H and cost The Authority control of WWE, which set up his WrestleMania 31 match against Triple H the following spring. A first WWE match did not come for roughly four months, and it ended in a loss.
The booking of that defeat frustrated plenty of fans at the time. Sting slid off WWE television for several months afterward before a short return in the fall.
Sting suffered a serious neck injury in September 2015 during a WWE Championship match against Seth Rollins. The injury looked in the moment like the end of his in-ring career.
Sting signed with AEW in 2021 and wrestled a cinematic match at Revolution that many viewed as a fitting farewell. The Icon kept wrestling anyway.
Retirement finally came at AEW Revolution in 2024, where Sting and Darby Allin beat the Young Bucks to close his career as one-half of the AEW World Tag Team Champions. A run of 25 additional matches followed the 2021 return before that final night.
Undertaker versus Sting is the greatest WrestleMania match that never happened, and the man with the 25-2 record just confirmed it should have. Two of the most iconic characters the business ever produced, both trading on silence and menace and presence, kept apart by one gut call. McMahon built an empire on instinct, and instinct is exactly what buried this one. The visual alone would have stopped the world cold.
Sting found an ending anyway, riding out on his own terms with Allin rather than falling in a WWE ring. Undertaker got his farewell too. What neither man got was the match carved into every fan’s imagination for a decade, and that hole never gets filled now. Some dream matches wait too long. The clock ran out on this one.
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