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Sting vs Undertaker: Could Legendary Match Still Happen in AEW/WWE?

Even after Sting's retirement match at AEW Revolution, could he suit up again one last time if that opponent was The Undertaker in AEW or WWE?

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As Sting wraps up his in-ring career at AEW Revolution on March 3rd, there's always that lingering question of what's currently billed as his "retirement match" would be it, as wrestling retirements don't always stick, especially when that itch comes back for those like the late Terry Funk. After all, it seems like the current white whale of wrestling dream matches is if the 64-year-old Steve Borden and the 58-year-old Mark Calaway, aka WWE's The Undertaker, could battle for a one-off epic final match. As far as in-ring legacies go, Sting has done it all wrestling for almost every single major US promotion during his nearly four-decade career. He never wrestled for ECW, but would he have fit in? Not only was he the face of WCW, but you can also argue that he was also the franchise in TNA. You can argue how WWE's overly cautious ways ruined his run with the company, but unfortunately, he was on the shelf for a large part of it, not to mention one of the injuries that occurred during his match with Seth Rollins, the current World Heavyweight Championship that was also the final one he had for the company. Let's circle back if a match could happen in, say WrestleMania 41 in 2025 or even later, given Sting and Undertaker's ages and the time needed to prep.

Sting renders his legendary WWE run meaningless while plotting to retire a second time on AEW Dynamite
Sting renders his legendary WWE run meaningless while plotting to retire a second time on AEW Dynamite

How Older Wrestlers Like Sting Have Sustained Their In-Ring Careers Working with Younger Talent

If you look at Sting's current run in AEW, he's been a mentor figure to Darby Allin, regularly tagging with him. The fact is, Sting can't carry a singles match the way he used to in WCW and TNA. Putting younger talent with older is natural when it comes to wrestling because the older and typically, slower talent can get their spots in without having to stay for longer stretches to mask any mobility issues. The same goes for the Undertaker, especially when you look at the long breaks between the several surgeries and time recuperating he's had between his final matches for WWE. While he's had some classics against Shawn Michaels in their WrestleMania bouts, his final matches include the 2018 Crown Jewel reuniting with his Brothers of Destruction partner Kane against D-Generation X's Michaels and Triple H, and his WrestleMania 33 bout with Roman Reigns were pretty atrocious. Keep in mind the Crown Jewel tag match was between four seasoned veterans with decades of experience, multiple championships, and main events among them. Not even the younger then-33-year-old Joe Anoai could salvage an otherwise sloppy WrestleMania match. I'm okay with Taker's final opponent being AJ Styles in that Boneyard Match at WrestleMania 36 as it set out to let the Deadman go out on top and not in a heavily demanding manner.
Escape The Undertaker. The Undertaker in Escape The Undertaker. c. Netflix © 2021
Escape The Undertaker. The Undertaker in Escape The Undertaker. c. Netflix © 2021

Also, before I go on, Borden and Calaway did tango back in WCW when the latter was "Mean Mark Callous" in a squash for Sting before Calaway solidified himself in WWF as Taker. Not that the WWE Hall of Fame has ever stopped any wrestler from competing, but could Sting and Taker squeeze a classic bout for the ages? Well, let's reexamine another wrestler who came back after a long time away from the ring Stone Cold Steve Austin, in 2022's WrestleMania 38 against Kevin Owens. Before his proper farewell match with WWE (for now), Austin last wrestled for the company defeating The Rock at WrestleMania XIX in 2003, citing his ongoing neck issues. He would become a part-time and behind-the-scenes character off-and-on since then, currently hosting his podcast and talk series Broken Skull Sessions. If you look carefully at his match against Owens, it was hardly a technical bout, nor did the then-57-year-old take anywhere near the bumps as the much younger then-37-year-old Kevin Steen. Again, older versus younger opponents typically work better.

This begs the question, could Sting vs. Undertaker work in 2025 and beyond? Well, if it were AEW (or in Japan), then I would say they would do that in a heartbeat, but Calaway is probably too loyal to WWE for that to happen. He's hardly in the same condition as guys like AEW's Chris Jericho and Adam "FKA Edge" Copeland, who are still capable talent and not riddled with Taker's physical issues. Could WWE book Sting/Taker for WrestleMania 41? I can see Borden giving WWE another shot for that one-off, working with wrestler-turned-executive Paul Levesque (Triple H) again, but like their bout in WrestleMania 31, which was riddled with run-ins from the nWo and D-X, it won't go as fans expect. I see them with, at minimum, a plus one or more with a tag match, triple threat, or fatal four-way, with younger talent carrying the bulk of the work far more likely than a one-on-one bout.

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Tom ChangAbout Tom Chang

I'm a follower of pop culture from gaming, comics, sci-fi, fantasy, film, and TV for over 30 years. I grew up reading magazines like Starlog, Mad, and Fangoria. As a writer for over 10 years, Star Wars was the first sci-fi franchise I fell in love with. I'm a nerd-of-all-trades.
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