Why did Undertaker vs. Sting never happen in WWE?

"It freakin' fell through the cracks! I still shake my head in amazement at how we dropped the ball on this one!"

The above statement is from one of my insider WWE confidants. The company has employed him for over 20 years. No, I won't reveal his name, as that would be the end of this very exceptional relationship we have shared.

I called him a few days ago as Sportskeeda Wrestling's Content Manager Riju Dasgupta asked me why a match between The "Phenom" — The Undertaker and The Icon Sting never happened.

For one of the first times in my 50 years as a "pro wrestling expert," I was unable to give a definitive answer. My source continued to give his view, but it really didn't satisfy my curiosity, so I pressed him a bit harder.

"Okay," he said. "I don't know exactly why it fell through the cracks, as I said before, but there are a few reasons I have heard tossed around the office here that make some sense. The first one is that neither of them would want to lose and a count out or draw would anger the fans. The other is that when the idea was being discussed, they were both toward the latter part of their careers. Do we really want to see them not at their best? I mean, look at what happened with 'Taker and Goldberg. If that match happened eons before that there wouldn't have been what turned into a big botch after all. It would have worked when they were in the days of the Monday Night Wars for sure, but of course that could not happen. Personally, I would have loved to see that match with the two of them in their primes."

I decided to reach out to my friend Jerry "The King" Lawler as he has been around the WWE machine for ages:

"I don't know Bill," Lawler told me. "I usually have an answer, but why this didn't happen is a mystery to me. What a box office and pay-per-view that would have made. It would have made a fortune!"

Keeping this in mind, when Sting came to WWE, The Undertaker was locked in a feud with Brock Lesnar, and Sting was put in with Triple H.

"Keep that in mind," my source told me. "WWE has always made long-term plans. The two of them were already with other opponents so the timing was awful.

When queried about a match against the Undertaker, Sting said:

"I wanted that to happen. I was very clear publicly, and I was very clear with WWE, as well. I wanted my last hurrah against Taker," said Sting. "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." [H/T Sports Illustrated]

The Undertaker did a 2020 interview with Comicbook.com where he said:

"Well, in this world, you never say never, but I think as great as it sounds on paper... And it does, I mean obviously that is a super marquee match, right? 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 noted. "So like you said, There's so many people that are clamoring for that match that I just don't know that the match could deliver on the people's expectations."

In my opinion, Undertaker vs. Sting would have made an excellent cinematic story, but honestly, it's such a shame we lost the match we all hoped to see.

When we think about some of the most wanted dream matches that never happened, this match -- The Undertaker against Sting is number one on my list!