WWE Never Held The Undertaker Vs. Sting Because Vince McMahon Didn't Want To Do It

Of all the dream match scenarios in professional wrestling history, none come bigger than a clash between The Undertaker and Sting, with fans clamouring for such a match for the best part of 20 years.

But as much as the fans wanted the match, one man in particular didn’t - Vince McMahon. The Undertaker himself spoke of the potential match on his Six Feet Under podcast, with the ‘Deadman’ revealing McMahon’s resistance to booking the bout:

"That would have been huge box office, it just didn’t work out. He [Sting] had a short run in WWE and Vince [McMahon] didn’t want it. For whatever reason, I don’t know what it was. He just didn’t feel it. Everybody else was like, ‘People have been clamouring for this match for quite a few years.’ A year or two into that character change, people were already sending me artwork with the billboard or poster. It just never worked out. Then, when he got there, the match would have been good, but I don’t think it would have lived up to the expectations that people have for it. People always think about things in a certain sense. I think they thought in their mind of Undertaker 2007-2008 vs. Sting. It was later on than that. I can say, I was way on the backside of what I was going to do when he got there," said Undertaker.

Vignettes hyping The Undertaker’s return in early 2011 had many fans believing Sting was coming into WWE, but ‘The Icon’ wouldn’t make his way to the company until Survivor Series 2014. Sting finally hung up his boots at AEW Revolution 2024.

Sting stated in May 2021 that he wanted his "last hurrah" to be against The Undertaker and he lobbied for the match within WWE. It just never happened, however.

H/T: Fightful