WWE Fantasy Matchups: Sting Versus The Undertaker

Sting & Taker
Sting vs Undertaker Photo Credit: WWE / Sports Al Dente Illustration

When Sting’s long-awaited WWE debut finally happened in 2014, we thought we might finally see Sting vs The Undertaker at WrestleMania. However, we were rather treated to Sting vs Triple H at WrestleMania 31 that included a fun spot with D-Generation X and the NWO.

Even though the WWE Universe didn’t see the dream matchup that sits atop most lists, Sports Al Dente always delivers. In our second installment of WWE Fantasy Matchups, we will go through what a Sting/Undertaker match would have looked like.

Tale Of The Tape


Height: 6’2″

Weight: 250 lbs

Signature Move: Stinger Splash

Finishing Move: Scorpion Death Drop / Scorpion Deathlock 

The Undertaker

Height: 6’10”

Weight: 310 lbs

Signature Move: Choke Slam / Old School

Finishing Move: Tombstone / The Last Ride / Hell’s Gate

The Buildup

Undertaker and Sting are different breeds when it comes to professional wrestling superstars. They are a couple of the most recognizable characters in the history of sports entertainment but outside of that scope not very many people would know their name.

The rarest and perhaps best thing about them is that they have each spent almost the entirety of their careers as one persona with one company. Even though the latter fact is what kept these two apart it has cemented their legacy.

Sting debuted for NWA/WCW in 1987 and quickly earned a name for himself. Sting would win his first Heavyweight Championship in 1990.

He would go on to feud with megastars like Ric Flair, Rick Rude, and the NWO throughout the 90’s while capturing every major championship in WCW.

As is true with any professional wrestler who has reached the top, Sting realized he needed to change with the times. His trademark blonde hair and brightly colored tights had grown stale and the crowd was used to it. As the late 90’s approached and the NWO was running rampant, WCW stars like Lex Luger, Randy Savage, and eventually, the fans had accused Sting of being on the NWO’s side.

The betrayal of WCW caused Sting to turn to a dark place and completely reinvent his character. His would wear a long black trench coat and paint his face all white with black stripes. Very much the look that many know of Sting today. Sting’s rivalry with the NWO and dropping from the rafters to attack them helped WCW stay ahead of WWE in the Monday Night Wars.

As WCW folded and was ultimately bought out by Vince McMahon, Sting’s future was in the air due to WWE choosing not to buy out Sting’s contract. The two would enter negotiations in 2002 but no agreement was reached. He would arrive in TNA in 2003 and eventually became one of their primary attractions, along with a few other former WCW and WWE stars.

While in TNA, Sting would have memorable rivalries and matches with some of the best sports entertainers in the world like Kurt Angle, AJ Styles, and Samoa Joe. He would be a five-time Heavyweight Champion during his TNA tenure and won the TNA Tag Team Championships once with Angle. He would be inducted into their Hall of Fame in 2012.

After leaving TNA in 2014, Sting, the most talented and infamous wrestler to never step foot in a WWE ring, was about to leave his footprints all over it. He would make his long-awaited WWE debut during the 2014 Survivor Series.

This debut would set up a match with Triple H at WrestleMania 31, when many fans, if not all, wanted to see Sting and The Undertaker face off once and for all. Speaking of The Deadman.The Undertaker debuted in WWE with his then manager Brother Love in 1990, ironically at Survivor Series.

He would defeat Hulk Hogan for his first WWE Championship exactly one year later at the 1991 Survivor Series. At the time, he was the youngest WWE Champion in history. He would have a series of controversial matches with Hogan over the WWE Championship which led to the title being vacated, leading to the 1992 Royal Rumble match winner being crowned the new champion.

The Undertaker solidified himself as the new dominant big man the rest of the early 1990’s by earning big victories over men like King Kong Bundy, Kamala, and Yokozuna. He would win his second WWE Championship six years after his first when he pinned Sycho Sid at WrestleMania XIII.

The Undertaker took on a more satanic version of his character in the late 90’s and early 2000’s. He and his faction, The Ministry of Darkness, would strike fear and panic into their foes. After a stint as Tag Team Champions with The Big Show, he would take time off to heal an injury.

Similar to Sting, The Undertaker would reinvent himself and upon his return, debuted his new gimmick as the American Badass version of The Undertaker. He dropped all of his dark or demonic characteristics and instead wore sunglasses, leather pants, and rode a motorcycle to the ring.

This version of The Undertaker was pretty much the real-life Mark Calaway turned up to 11. Eventually, he would cut his signature long hair and sport a crew cut.

The Undertaker would keep this persona for about three years until his “brother” Kane would interfere in a Buried Alive Match between The Undertaker and Vince McMahon at the 2003 Survivor Series causing Taker to lose. The Undertaker would again be off WWE television for an extended period of time. The WWE Universe would not see him again until March 2004, WrestleMania XX.

The Deadman version of The Undertaker returned to face Kane at the twentieth WrestleMania where he would also be reunited with his longtime manager, Paul Bearer. The Undertaker would remain in the main event picture for the remainder of his career.

He is a seven-time WWE Heavyweight Champion, six-time WWE Tag Team Champion, one-time WCW Tag Team Champion, one-time Hardcore Champion, and won the 2007 Royal Rumble.

During the most intense and entertaining era in professional wrestling Sting and The Undertaker stuck with their companies through thick and thin. They will forever be entrenched in the history of WCW/TNA and WWE respectively. These two never crossed paths in a main event scenario that would have been the biggest draw in a decade. It is finally time to look at the match! Sting versus The Undertaker!

The Match

The arena goes dark, a crow caws, a scorpion appears on the Titantron, and the beat of drums begin to emanate from the speakers as a lone spotlight shines on the top of the ramp. Finally, The Man They Call Sting makes his way toward the ring.

With his red trench coat, Sting walks to the ring, signature baseball bat in hand. As he solemnly climbs the steel ring steps, he enters the ring as his hordes of fans let their hero know they are behind him during his fiercest foe to date.

Darkness befalls the ringside area and beyond once more. This time an eerie chill fills the air. A gong begins to reverberate the entire area and rattles the rafters. The low rumble from the creatures of the night morphs into a raucous roar as their Lord of Darkness appears amid the mist at the top of the stage.

The Deadman appears to glide down the ramp as his round felt hat covers his brow and eyes. He ascends the steps and stops at the top. He lowers his head ever so slowly. He slowly lifts his arms into the air as the arena is slowly reilluminated simultaneously.

The two icons glare at each other from across the ring. As the bell rings, the two stand stoically. Sting rears his head back and lets out one of his symbolic “WOOOOO”s.

Undertaker reciprocates with his patented death glare as his eyes roll into the back of his head.

The two square off, going into a collar and elbow tie up. The taller Undertaker puts Sting in a side headlock but the Stinger is able to use the ropes to send ‘Taker across the ring. Upon Undertaker’s rebound, he meets Sting in the middle of the ring as both men stalemate against each other. Sting bangs on his chest showing he will not back down in fear.

The Match Continued

The Undertaker responds with his lightning fast jabs to the body and head of his opponent, backing Sting into the corner. The Undertaker twists Sting’s arm over his head, climbs to the top rope, and hits Old School.

With the WCW legend lying face down on the mat, Undertaker goes to lift him back onto his feet. While doing so, Sting bursts up and delivers knife edge chops to ‘Taker’s chest. With Big Evil stumbling, The Vigilante hits a standing dropkick which puts his adversary on his back.

Sting is able to lift Undertaker to his feet and Irish whip him into the turnbuckle but the once American Badass bounces out and hits a clothesline on Sting, sending him rolling out of the ring to gather himself. The Undertaker reaches over the top rope and snatches Sting by his hair, Sting is able to use his leverage and pulls ‘Taker outside.

Sting pulls Undertaker to his feet, but before he lands another chop, he is met with a stinging right hand. Undertaker lifts Sting onto his shoulder and drives him head first into the outside ring post. With Sting still slung over his shoulder, he places him on the ring apron. He climbs onto the apron himself and nails his huge leg drop.

Seemingly in full control, Undertaker returns to the inside of the ring to put the finishing touches on Sting. He signals the end with the throat slash.

He gets Sting in the Tombstone position but Sting is able to flip Undertaker over and reverse the hold and plants his own piledriver on The Deadman.

With the crowd on their feet, he goes for the pin but Undertaker kicks out at the 2.5 mark. Sting gets his foe to his feet, slings him into the turnbuckle, and hits a Stinger Splash.

He then gets behind Undertaker and is able to execute his Scorpion Death Drop.

Immediately covering The Undertaker, it seems inevitable that the match is over, however, The Phenom is able to beat the three count on what has to be pure instincts. A bewildered Sting then goes for a Scorpion Deathlock but Undertaker is able to lock in his Hell’s Gate.

Sting being the seasoned veteran he is, realizes he can attempt a pin while in the hold. With the referee counting, Undertaker releases the hold to avoid the pinfall. Both men lie on the ground, recuperating. All of a sudden Undertaker sits up. He climbs to his feet and is clearly fed up with toying around. He awaits Sting to get to his feet, as soon as he does ‘Taker grabs a hold of his throat and hits a Choke Slam.

Undertaker sets up Sting for a Tombstone once more and this time he hits it. As Undertaker covers Sting with his hands over his heart, Sting miraculously kicks out as the fans cry out in shock.

The Undertaker realizes the only way to get Sting down for three is to send him on his Last Ride.

This time, there is no kicking out. Undertaker covers Sting for the one, two, three and is able to lay claim as the true Icon. As Undertaker’s music plays, he rolls out of the ring and staggers up the ramp after a brutal battle. Finally, Sting makes it to his feet, greeted with a standing ovation from the crowd as they show their appreciation for his valiant effort.We never got to see how an actual match would play out between the two immortal figures but now we can all have a bit of a glimpse of what could have been. Thanks to our Twitter voters, our next installment of WWE Fantasy Matchups will feature The Great One versus Mr. WrestleMania. The Brahma Bull versus The Heartbreak Kid. That’s right, The Rock versus Shawn Michaels!