Sting vs. The Undertaker: The Truth, Lore, and Fantasy of the Dream Match That Never Was


The ultimate "what if" scenario in professional wrestling history. (Credit: WWE)

I’m not entirely sure when the legend of the fabled Sting vs. The Undertaker match began. Perhaps it was the idea of the “Icon vs. Phenom” that gave fans hope that something would rise from the ashes of the disappointing “Invasion” storyline as WCW and ECW stars migrated to the WWE roster post-sale. Perhaps it was the idea that two of the darkest characters in the history of our great sport could finally come face to face in the ring together, giving the long awaited stare down. The crowd pop this moment would have received could only be comparable to the one received at the beginning of the greatest WrestleMania match of all time, The Rock vs. Hulk Hogan at WrestleMania 18.


Think about Sting vs. The Undertaker like the Manny Pacquiao vs. Floyd Mayweather fight, except in professional wrestling. Two titans, at the top of their field, well respected across multiple generations of superstars in multiple promotions, certified legends. It was the match that should have happened, and for whatever reason, didn’t.


Every self-respecting wrestling fan, including myself, held out immense hope that eventually, somehow, this would happen. Even WWE was building on the hype, teasing the match every opportunity possible. Whether it was physical limitations, financial disagreements, or something as simple as creative differences, the match never came to be. Wrestling fans everywhere sighed loudly at the loss of a dream that seemed so close to coming true.

One of the more creatively impressive things to come out of entertainment during the pandemic is the “cinematic match” in professional wrestling. Like a mini movie, fans can experience a new way of viewing the competition. The match takes place in a separate location from the usual in ring performance. The predetermined result is the same, but the action can happen literally anywhere: back alley, graveyard, even moving back and forth between time.


The possibilities with Sting and The Undertaker in the cinematic realm were limitless. Dark, demonic, evil – all encompassing, all engrossing. As I watched the AEW Street Fight, and reflected on WWE’s recent cinematic matches at WrestleMania 36, I asked myself...


"How the hell could Vince McMahon pass on this opportunity?"


I couldn’t help but ponder the missed opportunity of a cinematic match between Sting and The Undertaker, and how incredible it could have, and should have, been.


Sting, a golden boy babyface during the early 1990s, became the unlikely and unwilling savior of WCW as the NWO ran through the roster. Wearing black and white face paint, a more than obvious ode to the classic character played by Brandon Lee in The Crow, and wielding a black baseball bat under his trench coat, Sting was the ultimate anti-hero. He is considered by both fans and historians to be the greatest performer in WCW's history.

Sting during the AEW Street Fight cinematic match, during AEW Revolution. (Credit: AEW)

The Undertaker stood as the only superstar in any promotion who could match Sting’s intensity, drive and darkness. The Undertaker, legendary for his longevity, as well as the storied "Streak" where he remained undefeated at WrestleMania for 21 straight matches, is considered one of, if not the, greatest performers in WWE history. Not only do these men share dark, mysterious, otherworldly personas, they were both fiercely loyal to their companies, and could always be counted on as the respective franchise players in their organizations.

The Undertaker during the Boneyard Match, from Night 1 of WrestleMania 36. (Credit: WWE)

It seemed only fitting that, as the doors of WCW were closed for good and the folded promotion was purchased by WWE, Sting would make his way into the fold, working with a who's who of talent including Triple H, John Cena, and Kurt Angle. However, to the surprise of most fans, Sting passed on the opportunity to join WWE in 2001, and again in 2003 when he signed with TNA for a long term contract. Fans continued to fantasize over the idea of a Sting run in WWE, stuck on it like a drug and unsatisfied no matter how many times we played the result out in our minds. We all knew exactly how it should’ve started, too. It was the only acceptable option.


There were many start and stop motions to get Sting in the ring with The Undertaker along the way, and fans finally thought they’d get the matchup in 2014, when Sting officially signed with WWE for the first time in his career. Most of us in our hearts knew for sure this was it. We were finally getting what we'd been waiting for. The final payoff in the WWE vs. WCW war.


Instead of The Undertaker, Sting was pushed into a feud with the heel stable, The Authority, which produced an exciting and solid feud. Sting again played the unwilling champion of the WCW brand. The feud was capped by Triple H scoring a controversial win over Sting at the only WrestleMania match he would ever wrestle in. Taker ended up in an equally solid feud that Mania season with Bray Wyatt. Fans hoped the pendulum would swing back around towards The Undertaker showdown once this business with The Authority was complete.

Sting wrestles Seth Rollins during Night of Champions in 2015. (Credit: WWE)

Sting’s in-ring career came to a sudden and abrupt conclusion during his only challenge for the WWE Championship, in a match with Seth Rollins at the 2015 Night of Champions pay per view. Rollins delivered two "buckle bombs", a dangerous move where a wrestler takes his opponent and powerbombs them into the turnbuckles, to Sting towards the end of the match. The force of the buckle bombs, and subsequent snapping back of Sting's head and neck on impact, exposed a condition not previously known to him – cervical spinal stenosis, a diagnosis that has derailed other wrestlers’ careers, including most famously Edge, until the 2020 Royal Rumble saw his return to wrestling.


At 61, Sting only has so much left in the tank before age, or potential serious injury, catches up to him. It’s not clear if Sting underwent the same surgery procedure that Edge did to allow him a clear bill of health to return to wrestling. After the pandemic set in and the wrestling landscape was forced to adapt—a cinematic match was not only a reality, but the clearest path to get these titans together. The Undertaker had completed an incredibly successful and well received cinema match, called The Boneyard Match, where he competed against AJ Styles in a graveyard during Night 1 of WrestleMania 36.


It seemed only logical that the next outing for the Phenom in this setting would be against the Icon. All that was left was to green light it. Sting finally would’ve gotten his shot against the one competitor to match his darkness. The Undertaker, out to show he is the true Phenom and Icon in sports entertainment, would finally have the chance to vanquish the one chasing him for more than a decade.


During a recent appearance on "AEW Unrestricted", Sting pitched the idea of a cinematic match with The Undertaker to WWE officials before getting into negotiations with AEW:

“I was pushing to get a cinema-style match with Undertaker. For probably a litany of reasons, it just wasn't going to happen. When Tony (Khan) called and spoke with me, he said, 'Are you interested in doing cinema-style matches?' I said, 'Yeah, I am.' I'd like to come back and do that and not disappear with my tail between my legs. I don't have to go out on top, I'd like to go out in a positive light."

Taker commented on the legend of the match on the IGN YouTube channel, after a fan asked directly whether it would ever happen:

Only a handful of people know for sure what the reasons behind the decision to pass on the cinematic match between Sting and The Undertaker, but after watching the Street Fight, the Boneyard Match and the Firefly Fun House Match, it’s apparent that AEW succeeded with Sting where WWE should have. Unlike the Pacquiao/Mayweather fight, which left fans feeling let down by not reaching the hype it created, the cinematic match format presented a rare opportunity. The match would’ve been the delivery of the most hyped sports entertainment showdown of our generation, while perfectly masking the limitations that both performers felt would disappoint fans who had waited so long for this to happen.


The AEW Street Fight provided the depth and latitude for a character like Sting to run one last shot, one last crescendo in one of the most storied and successful careers of all time. WWE could’ve easily leveraged the foundations of the Boneyard Match to build something truly memorable with the Undertaker, while giving fans the business with elements pulled from the psychologically impressive Fun House matches. Hell, they could’ve merged to the two matches together and created some truly incredible content.


Think about it: Sting is tortured by the idea of not being able to face Taker one on one, with Wyatt purposefully stretching the limits of his mental well-being. Each step in the match gets him closer to Taker, only to have it snatched away one more time. Sting, obsessed with his legacy, is ultimately forced to relive the Monday Night Wars and his showdown with Hollywood Hogan. Now a bitter, old, broken man with a god complex, Sting sees the truth – it was never about the salvation of WCW, or triumph over Hogan, or the missed opportunity with Taker – he’s only ever been in it for himself, and his legacy. What he needed to prove to himself. Fiend attacks, Taker delivers a tombstone to a stand in Sting, 1, 2, 3. Game over.

I will forever wonder how this all would have panned out, what magic we would’ve been in store for, and how disappointing it is that the potential of this cinematic match was never realized. Sting vs. The Undertaker will remain the greatest unanswered question in sports, and continues to live on in the theater of the mind for millions of fans who asked “what if?”


Adam Barnard is a staff writer for Kulture Popped, and purposefully keeps his Sting and Undertaker action figures next to each other on the shelf to help promote the idea that this match could eventually still happen. You can check out all of his content and projects by visiting ThisisGoober.com.