The Undertaker vs. Sting is one match that many fans were desperate to see.
With both Hall of Famers each having their own unique, dark personas and being main event stars of their respective brands in the late 90s, many hoped that The Phenom and The Icon would clash in the near future following the WCW buyout by WWE. However, while multiple top names would make their way over to the worldwide leader of sports entertainment during the Invasion angle and stars such as Hulk Hogan and Goldberg signed within the next couple of years, Sting would delay his appearance until 2014. The Icon would instead sign with TNA from 2003 to 2014.
Sting’s decision to bypass WWE was made as he was not confident in how he would be positioned within the company following the mistreatment of other WCW stars during the Invasion angle, with the rivalry between The Rock and Booker T being used as the main example.
November 2014 to September 2015 would be the only time that The Icon would be an active competitor in WWE. At this point in time, The Undertaker was firmly on a part-time schedule, not seen in-ring since his shocking loss to Brock Lesnar at WrestleMania 30. One year later the dream match was still not a possibility as Sting was scheduled to work with Triple H and Taker would wrestle Bray Wyatt. Referencing how The Icon did not trust Vince McMahon to book WCW stars properly, Sting did lose his debut match to The Game.
With Undertaker retired and Sting announcing his retirement at AEW Revolution 2024, this will always be a match that is a fantasy and not a reality. The Deadman was recently asked how he thought the match would play out while speaking with Bill Apter. Giving a humourous response to the hypothetical match, Taker revealed that he would have won:
“I’d have killed him,” he declared with a smile, “He’d have got a Tombstone brother, he’s going out after I’d planted him.”
The Undertaker Congratulates Sting
Despite never meeting face-to-face inside a ring in any promotion, The Phenom still has a ton of respect for the fellow Hall of Famer. Acknowledging what the former World Champion has done for the business, Taker congratulated The Icon on his longevity and accomplishments:
“Yeah I would love to say, Sting, congratulations man, on just a spectacular career. I mean just one true icon of our industry. He’s done everything, and like I said just the longevity of that character, just well done, and congratulations. I hope retirement is everything that you want it to be and you deserve everything you have.”
H/t to Wrestling Inc.