By far the biggest WWE dream match of all time that never happened is Undertaker vs Sting. The pair were the two stalwarts for their respective companies in the Monday Night Wars. Sting was loyal to WCW, fighting off the invading forces of the NWO. The Undertaker was loyal to WWE, as the leader of the Corporate Ministry. But for one reason or another, Sting vs Undertaker never happened.
But, the Icon Sting has revealed in an interview one reason why the match never happened during his time in WWE.
Sting vs Undertaker – Why it never happened

Sting in an interview
Sting revealed in an interview that he had pitched the idea of a cinematic match with the Undertaker to WWE, but there was little interest on WWE’s part.
“It wasn’t a goal of mine to get back in the ring. The only thing I thought I might do is have a cinematic match against Undertaker when I was with WWE. We weren’t able to come to an agreement”. Sting debuted in WWE in 2014, and had four matches before he “retired” due to neck injuries sustained against Seth Rollins.
Sting would return to wrestling in 2020, when he signed for All Elite Wrestling. He’s wrestled twice so far in AEW, with a third match planned for tonight’s AEW Dynamite.
Sting also said in an interview at “Starrcast” that he’s talked to Undertaker many times, and they get on well. Although, he said, they “never talked about it (the match between the two of them)”.
“I wanted that to happen,” said Sting. “I was very clear publicly, and I was very clear with WWE, as well. I wanted my last hurrah against Taker. For whatever reason, it just never materialized. To this day, I don’t know why. Maybe Taker never wanted to work with me. I have no idea.“
“I mean, I’ve had good conversations with Taker and we’ve always got along. I don’t know why the match never happened, but it should have happened. Because it wasn’t going to happen, and I knew it, and that wasn’t the only reason why I left WWE, but it’s one of the reasons why I left. I wanted that one last match“
Interview with The Undertaker
The Undertaker has recently stepped out of character for the first time, and begun doing interviews. The most notable being his interview with Steve Austin on his WWE Network podcast. However, in an interview with Comic Book, Undertaker spoke about why he felt that he didn’t want the match to happen.
“But where I kind of differ from a lot of people is I look past the marquee value and I look on the ability to deliver.” The Undertaker said, “So like you said, there’s so many people that are clamouring for that match that I just don’t know that the match could deliver on the people’s expectations.“
“That’s a great match, but 10 years ago I think it could still happen and it could still be a stellar match. I’m just not sure at this point that it could deliver on the hype.”
Sting vs Undertaker
Sting and the Undertaker actually DID have a match!
In WCW in 1990, then NWA Heavyweight Champion Sting defended his championship against a tall, ginger wrestler from Texas. That man was “Mean” Mark Callous, who would later move to the WWF and take on the persona of “The Undertaker”.

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