Add as a preferred source on Google The Undertaker has once again blamed Vince McMahon for never booking one of the most requested matches in WWE history.
Speaking on the July 29 episode of Six Feet Under, The Deadman discussed facing Sting and McMahon’s decision not to book the match.
“Obviously, people had already been clamoring for that match for a long time, and it seems like a no-brainer. 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-view.’ 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, Sting vs. Undertaker. Again, he obviously knows more about business than I do, but that one just seems 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’ve loved to have been able to have that match.
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 why.’
It is what it is, man, I guess. 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.”
The best chance came at WrestleMania 31 in 2015. Sting made his official WWE in-ring debut against Triple H, while The Undertaker faced Bray Wyatt. The two veterans were on the same flight after the event and talked about the match, which still had not been booked.
Sting wanted it, too. In 2016, he told WWE.com that he wanted to wrestle at one more WrestleMania before retiring and that The Deadman was the opponent he had in mind. The neck injury Sting suffered against Seth Rollins at Night of Champions in 2015 all but ended that possibility in WWE.
By 2020, however, The Undertaker had taken a more cautious stance, saying he had never received a serious proposal and that a match at that point might not live up to expectations built over decades.
Sting and Mark Calaway did face each other on September 1, 1990, in Greensboro, North Carolina. Then wrestling as Mean Mark Callous, the future Undertaker lost to Sting in a defense of the NWA World Heavyweight Championship.