For decades, professional wrestling fans clamored for a showdown between The Undertaker and Sting, a “dream match” that stood as the ultimate “what if” scenario in the industry. As the respective “consciences” of WWE and WCW during the heated Monday Night Wars of the 1990s, the two icons mirrored each other in loyalty, mystique, and longevity. However, despite both men eventually being under the WWE banner at the same time, the match never materialized.
What The Undertaker vs. Sting Could’ve Been
A new report has shed light on exactly why the bout was kept off the card, placing the decision squarely at the feet of former WWE Chairman Vince McMahon. Speaking on “Wrestling Observer Radio,” Dave Meltzer explained that the reason the two legends never shared the ring came down to McMahon’s personal assessment of Sting’s star power relative to The Phenom.
According to Meltzer, McMahon did not view the matchup with the same reverence as the fanbase. While audiences saw a clash of titans, the WWE boss reportedly did not perceive Sting to be on the same tier as his own creation, The Undertaker.
“That’s a Vince call. And in hindsight, I guess the answer is no. He never saw the big thing in it that a lot of people did. He could have done it. Many people would have wanted him to do it. I don’t think he saw Sting at the level of Undertaker. And he didn’t do it,” Meltzer said.
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Their Careers
The window for the match seemed to open in 2014 when Sting finally signed with WWE after spending years as the face of TNA Wrestling following the collapse of WCW. His arrival at “Survivor Series” sparked immediate speculation that a confrontation with The Undertaker was imminent. However, creative plans took a different direction.
At “WrestleMania 31” in 2015—the event many pinned as the ideal stage for the bout—WWE opted for different opponents for both men. The Undertaker defeated Bray Wyatt, while Sting competed in his first-ever WWE match against Triple H. That bout, which featured interference from D-Generation X and the nWo, was presented as a nostalgic final battle between WWE and WCW, ultimately ending in a loss for “The Icon.”
Sting’s in-ring career in WWE was cut short later that year following a severe neck injury sustained during a match against Seth Rollins at “Night of Champions.” He announced his retirement at the 2016 Hall of Fame ceremony, seemingly closing the door on any future bouts.
However, Sting defied the odds by returning to the ring in AEWyears later. He enjoyed a celebrated run in Tony Khan’s promotion, competing in tag team matches alongside Darby Allin and maintaining an undefeated streak. Sting officially retired on his own terms at “AEW Revolution 2024,” finishing his career without ever locking up with The Undertaker.
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