Fantasy Matchup Series: Sting vs The Undertaker

Rob returns with quite possibly the ultimate fantasy match up: Undertaker v Sting!

Fantasy Matchup Series: Sting vs The Undertaker

The next bout we shall be exploring is a much talked about dream match. Both men could arguably be considered to be the conscience and backbone of their respective companies. They had many similarities, particularly the aura and mystique that surrounded them. The two wrestlers that I am referring to are Sting and The Undertaker. These highly accomplished wrestlers need no introduction to a wrestling fan. Both names are synonymous with greatness, longevity and loyalty. The Undertaker, until his recent retirement, was a mainstay of the WWE since the early 90's. Sting, or “The Franchise of WCW”, faithfully served that company from 1987 until the very end of its existence in 2001. 

It is extremely difficult to summarise the careers of two incredible men without the fear of trivialisation. Both deserve several articles to even begin to scratch the surface of their many and great accomplishments in the world of professional wrestling. If there was a wrestling Mount Rushmore, then Sting and Undertaker would definitely be on it. But, for the purpose of this series, I will attempt to give a concise, yet respectable rundown on their careers. 

The Undertaker first made his presence felt in 1990, appearing at the Survivor Series as part of Ted Dibiase’s Million Dollar team. A near seven foot monster, billed from Death Valley, and weighing over three hundred pounds, he was quite a sight to behold. He would legitimately frighten children in the audience with his ghoulish appearance, black, macabre attire and almost otherworldly mannerisms. His in-ring performances were a mixture of methodical reserve and explosive offence. He would slowly grind his opponents down, and finish them off with his signature Chokeslam and Tombstone Piledriver finishers. When he needed to, he could fly through the air, launching himself at his opponents over the top rope and onto the floor. For a man of his size, he was extremely agile, with another such example of this being his “Old School” manoeuvre, where he would literally walk the top rope while holding his opponent in a wrist lock, and then come crashing down on them with full force. 

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Perhaps Undertaker’s greatest achievement was his well documented and much celebrated winning streak at Wrestlemania. In an unparalleled record, he was undefeated in 21 Wrestlemania’s from 1991 to 2013. During his incredible 30 year tenure, he won the WWE title 4 times, the World Heavyweight title 3 times and captured the Hardcore Championship once. He also had a great deal of success in the Tag Team division. Over the years, and with four different partners, he won a grand total of 6 WWE World Tag Team Championships, and one WCW World Tag Team Championship. He won the Royal Rumble in 2007, was the winner of numerous Slammy and Wrestling Observer Newsletter awards, and all the while he re-invented himself to stay relevant. Over the years, his character evolved through various iterations to stay fresh, from the original Deadman in the early to mid 90’s, to the Lord of Darkness and his subsequent Ministry in the late 90’s, to his American Badass biker character in the early 2000’s. In 2004, he returned to his roots, bringing back the Deadman character, but retaining some elements of his American Badass persona. This new Undertaker, remained until his near retirement in 2020, when a true hybrid Undertaker surfaced for his last ever match - the Boneyard Match at Wrestlemania 36 against AJ Styles. This Undertaker was a combination of the Deadman and American Badass personas, with a sprinkle of his own real life persona thrown in the mix for good measure.   

“The Icon” Sting broke into the business a few years before Undertaker, with the character first appearing in Bill Watts’ UWF in 1986, where he teamed with Jim “Justice” Hellwig. In his early years, he wore a bright ring attire and colourful face paint, and was very popular with the younger fans. His style was fast and furious, mixing power and agility. In addition to his signature Stinger Splash and Scorpion Death Drop moves, he also performed the Scorpion Deathlock Sharpshooter hold, a move that gave him much success throughout his career. Championship wise, Sting won many accolades. He won the NWA World Heavyweight Championship twice, once in early WCW, and the other in TNA. He held the NWA World Television Championship once, twice won the WCW International World Heavyweight Championship and the WCW United States Heavyweight Championship, and is a seven time Tag Team Champion across various promotions. He also won the TNA World Heavyweight Championship four times, and is a six time winner of the WCW World Heavyweight Championship. 

He could easily be considered one of the all time greats of WCW, as he joined it in 1987 and remained there for another 14 years. During his time there, his character gradually shifted away from his colourful “surfer” gimmick, to a more dark and brooding, and later silent character. Taking heavy inspiration from the Eric Draven character in the movie The Crow, he started wearing black attire with white scorpions, black and white face paint, and could be frequently seen in the rafters of the WCW arenas, overlooking the rise of the New World Order. Occasionally, he would descend from on high using a harness, lowering himself into the ring and then laying waste to his nWo foes. 

Sting was part of many memorable moments, including the infamous Bash at the Beach 1996, where the nWo was first formed. He was part of the team that included Randy Savage and Lex Luger, who took on Scott Hall and Kevin Nash and a mystery partner, which turned out to be Hulk Hogan. After Hogan turned his back on WCW, Sting became the top face of the company, and spearheaded its fightback against the invading nWo. Also worthy of note, is Sting’s rivalry with “Nature Boy” Ric Flair. They had fought frequently over the NWA and WCW World Heavyweight Championships, and also had the distinction of facing each other on the first and very last edition of WCW’s Monday Nitro before the company folded in 2001. 

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The match between “The Icon” and “The Phenom” never happened for a variety of reasons. It was a combination of timing and also lack of willingness on the part of The Undertaker and WWE. Firstly, during the Monday Night Wars, with both being the cornerstones of their brand, it was inconceivable that the two characters would face unless one of them did the unthinkable and jumped ship to a rival promotion. That would be akin to Mick Jagger leaving the Rolling Stones, or Sir Alex Ferguson managing Manchester City - it just wouldn’t happen. 

A window of opportunity did open in April 2002, when Sting’s AOL Time Warner contract expired, and he entered into negotiations with Vince Mcmahon’s WWE. The move never transpired, and Sting joined TNA in 2003, where he remained until 2014. Sting revealed in an interview in the mid 2000’s that he ultimately did not join the WWE as he did not trust how his character would be used. He saw how the WCW alumni were treated, and how it was an uphill struggle for them to be accepted and respected, recounting a particular moment where The Rock buried Booker T by saying “who are you?”. That undoubtedly left a bitter taste in Sting's mouth, and he confessed in a WWE interview with JBL in 2016 that he viewed Vince Mcmahon’s interest in him with suspicion, feeling that Mcmahon wanted to use Sting to undermine WCW, instead of giving him a fair shot. 

Another chance for them to wrestle occurred in 2014, when Sting finally made the jump to the WWE. This was the best chance for them to do business, as he showed up at Survivor Series, which could have given them several months to put together an exciting programme for an epic encounter at Wrestlemania 31 the following year. In reality, it was decided that Sting was to face Triple H instead, and Undertaker took on Bray Wyatt. Despite both matches being of high quality, the WWE had permanently shut the door on any possibility of Sting vs Undertaker with their booking decisions that year. One could also argue that Sting’s suspicion of not being used properly was proven correct with having to put Triple H over at their Wrestlemania 31 encounter. While it was a competitve and exciting match, which also featured members of DX and the nWo finally coming face to face, the stigma of WCW could still be felt. JBL, who was on commentary that night, even went so far as to describe Sting’s tenure in WCW as being like “a big fish in a small pond,” and that now he was in WWE he was like “a minnow in an ocean”. 

The Undertaker himself has gone on record, explaining that a match between him and Sting “sounded better on paper” and that “the window had closed”. It is understandable why the Deadman would now be unwilling to lock up with another fellow aging wrestler, based on his experience working with Bill Goldberg in 2019. Undertaker was disappointed with how that match turned out, and it is obvious from the look of disgust on his face after the bell just how unhappy he was. That was a match that needed to happen 15 years ago, when both men were in their prime, and thus able to give the fans the match they wanted and deserved. Sting had pitched an idea of a cinematic match against Undertaker to WWE, but it was rejected, and Sting joined AEW shortly thereafter. Maybe some things are best left to people’s imaginations - and that’s where I come in. 

If I were to book these two to face each other, then it would have to be in their primes, at the height of the Monday Night Wars. Picture this for a moment: In an alternate reality where Glen Jacobs was cut from the WWE and thus never became Kane, the spot was filled by none other than Sting himself. In this reality, Sting shocked everyone by quitting WCW in the autumn of 1997, around the same time that Undertaker was feuding with Shawn Michaels. In their epic encounter at Bad Blood 1997, at the first ever Hell in a Cell match, Undertaker had the match won after cracking a bloodied, battered and bruised HBK full in the face with a steel chair. Then the lights go out. When they come back on, standing in the ring facing Undertaker is Sting, with a baseball bat in hand. The crowd explode as the two legends stare each other down, Undertaker wide eyed, and Sting with his signature haunted, determined look. Time seems to stand still, until the spell is broken, Undertaker attempts a clothesline, but Sting ducks and cracks the Phenom in the head with his baseball bat. The lights go out a second time, and when they come back on again, Sting is nowhere to be seen. Michaels then crawls over to Undertaker for the three count. 

Over the course of the next few months, Sting continued to taunt Undertaker, costing him several matches in the process. Undertaker repeatedly called out Sting, but “The Icon” did not answer the challenge, remaining silent, and residing, for the most part, in the rafters. For those who are unfamiliar, Sting used this tactic to great effect against the nWo, who never knew when Sting would appear from his perch and start swinging his bat. This psychological warfare was now being applied against Undertaker, who was fast beginning to tire of his antics. After costing Undertaker the match against Shawn Michaels at the 1998 Royal Rumble, the Phenom had finally reached breaking point. Shortly before Wrestlemania 14 on Monday Night Raw, with Sting again up in the rafters, Undertaker appeared on stage, his voice mysteriously magnified without the use of a microphone. Once again, he challenged Sting to face him, uttering only Sting's name angrily, and glaring up at the rafters. When Sting did not respond, Undertaker summoned a lightning bolt, which struck close to where Sting had been. Sting had disappeared from the rafters, but spotlights kept shining on what appeared to be multiple doppelgangers in the crowd. Incensed, Undertaker summoned more lightning strikes, but the faces vanished before each strike could find its mark. Then the lights went out. When they came back on, Sting was standing in the ring, staring at the Undertaker who was still on the stage. Sting grabbed a microphone and spoke for the first time on WWE television:

“You’ll have to get up a lot earlier than that to take the Stinger down! Undertaker, I’ve been watching you closely - and I’m not just talking about the months I’ve been here. I know who you are, I KNOW WHO YOU ARE ‘TAKER! I’ve also listened to you very carefully. You like to say that you are the reaper of lost souls, and are the Lord of Darkness. ‘Taker, I’m that one soul that you can’t take! You live in the dark, but you know nothing of darkness - not really. Well I’m here to show you! You want to face me at Wrestlemania? Bring everything you have - all your powers, all your strength, all your might - SHOW ME WHAT YOU GOT ‘TAKER! I’ll be waiting! IT'S SHOWTIME, FOLKS!”

Undertaker responded:

“Sting, your days are numbered. You have run from the reaper by using stealth, shrouding yourself under the cloak of your cowardice. At Wrestlemania, you’ll have nowhere to run, and nowhere to hide. I am the valley of the shadow of death, and you will fear the evil that resides within it! The only thing that you can do now is rest...in...peace!”

The match at Wrestlemania was one of spectacle, drama and controversy. Sting entered first, interrupting Pete Rose’s tirade against an angry Boston crowd. Sting lowered himself into the ring with a harness, and hit Rose with his Scorpion Death Drop finisher, much to the delight of the fans. Then Undertaker appeared, walking through the burning torches as his druids gave him a guard of honour. Both men wasted little time, and tore into each other almost immediately, exchanging right hands. Sting was first to blink, and Undertaker shot him off into the ropes, but Sting reversed and displayed his incredible strength with a military press slam. Undertaker sat up immediately, ducked a clothesline and hit Sting with a big boot. He then came off the ropes to deliver a leg drop, but The Icon rolled out of the way, and clotheslined ‘Taker out of the ring. The Phenom landed on his feet, and dragged Sting out of the ring and decked him with a hard right hand. He then pushed Sting against the apron and began pummeling him some more with lefts and rights to the body and face, and then beat Sting’s head against the steel steps and the announcers table. He then went for a chokeslam through the announcers table, but Sting fought out of it, and hit Undertaker’s head against the table, and hit him with a clothesline. Sting then climbed up to the top turnbuckle, and launched himself at Undertaker, catching him with a diving cross body. 

Recovering, Sting threw Undertaker in the ring and pinned him, but he kicked out at 2. Sting tried to lock in his Scorpion Deathlock, but Undertaker kicked him off. The Undertaker sat up, and when Sting charged for a clothesline, Undertaker back body dropped him outside the ring. When Sting got to his feet, he was hit by Undertakers suicide dive over the top rope, and then both men were down. The Phenom sat up, and threw Sting into the ring, hit him with a snake eyes on the top turnbuckle, and came off the ropes for a big boot. Sting was wise to it, and dropkicked Undertaker in the knees. Sting then started to take control of the match, and began chopping down the Phenom’s knees with shoulder blocks and knee stomps. Each time Undertaker tried a comeback, Sting would cut him off by hacking at his legs. The Undertaker was visibly frustrated by Sting’s tactics, which were proving to be extremely effective in keeping the big man off his feet. Eventually though, Undertaker managed to escape from Sting’s dissection of his legs, and hit him with a flying lariat. 

The Undertaker now had the momentum on his side, and began knocking Sting over repeatedly with hard right hands. But each time he hit Sting with a right, Sting would get up and come back for more, with a crazed look in his eyes. Undertaker halted his offence for a moment, and the two stared each other down. Sting stuck his tongue out as he let out a primal scream, and Undertaker rolled his eyes into the back of his head, before attempting another right hand. Sting ducked, and then began hitting Undertaker with right hands, chops and gut kicks in his trademark rapid pace, forcing Undertaker back into the corner. Sting then hit Undertaker with two Stinger Splashes. On his third attempt, Undertaker caught Sting by the throat, and gave him a hard Chokeslam. Undertaker’s knees buckled as a result of Sting’s earlier offence, and thus was not able to make the cover immediately. When he did, Sting managed to kick out at 2.9. Getting to his feet, albeit slightly unsteadily, Undertaker signalled for the Tombstone Piledriver. Sting countered this into his Scorpion Death Drop, and Undertaker kicked out just before 3. 

Sting attempted another Death Drop, but Undertaker reversed it, and got Sting up for a Tombstone, but then Sting slid out of it and got Undertaker in the Scorpion Deathlock. Undertaker fought several times to make it to the ropes, eventually managing to do so after a couple of minutes of agony. Sting returned to punishing Undertakers legs, hitting them with kicks and stomps. Sting then decided it was time to give Undertaker a Tombstone Piledriver of his own, but the Deadman reversed it and caught Sting with the Tombstone. Sting shocked everyone, including Undertaker, by kicking out. The Deadman signalled for another, and this time it was Sting who reversed it, hitting Undertaker with the move. Undertaker kicked out. 


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As both men lay exhausted on the mat, a commotion is caused as the crowd are distracted by someone coming down the aisle. Paul Bearer is hobbling to the ring, holding Undertaker’s urn, and looking concerned at the drama playing out. Bearer had not been seen on WWE television for almost a year at this point, with his last appearance being in April 1997 at Revenge of the Taker. Now he was back, and pacing around the ring, gesticulating to both men inside the squared circle. Undertaker sat up, and regarded Bearer for a brief moment, before returning his attention to Sting, who was already waiting for him. Sting attempts another Death Drop, but the Deadman fights out of it. Sting attempts a clothesline, but Undertaker ducks, and Sting hits the referee instead. Undertaker then attempts a Tombstone, Sting reverses it, but then Undertaker reverses again and finally hits the Tombstone. With no referee to count the pin, Paul Bearer steps into the ring, placing the urn into the middle of the squared circle, and motioning Undertaker to Tombstone Sting onto it. The Deadman takes him up on his offer, but as he was in the middle of picking Sting up, Bearer hits Undertaker with a low blow kick. Undertaker drops Sting, who recovers and smacks him over the head with the urn. The referee comes to, and begins to count. Undertaker kicked out just before 3, and Paul Bearer, enraged, hands Sting his baseball bat, which he had retrieved from under the ring. Sting charges at the Deadman, but he gets hit with a big boot. Then Undertaker chokeslams Sting, but the referee is dragged out of the ring by Paul Bearer before he could count to 3. Bearer decked the referee, and then climbed back into the ring to distract Undertaker. The Deadman hit his old manager with a hard right hand, knocking him to the floor, and then hit Bearer with the urn, busting him open. When he turned around however, he gets smacked straight in the face by a baseball bat shot from Sting. Undertaker crashes to the mat, and Sting waits for a second referee to come charging in and count to three. 

So, Sting wins the match, officially turning heel and allying himself with Paul Bearer in the process. I know this is a controversial finish that many of you will be unhappy about, and for good reason. For one thing, it meant that Undertaker's Wrestlemania streak never really became a thing. And another, it’s a WWE wrestler putting over a former WCW wrestler at the grandest stage of them all. For those that are not best pleased, hear me out. As previously mentioned, Sting was very hesitant to join the WWE as he did not want to be buried like other former WCW wrestlers. He lost to Triple H in his very first WWE match, which really highlights Vince McMahon’s attitude towards people who used to work for the competition. He was made an example of, just like he feared. Now in my alternate reality, my view is that getting his first win against Undertaker at Wrestlemania, especially with the controversial circumstances of his victory, would not only launch his career, but continue the programme with Undertaker throughout 1998. This would create many more competitive matches between the two as they battled for ultimate superiority.  If you’ll pardon the intentional pun, I wrestled with the outcome of this match for quite some time. Ultimately, I decided against a single or double DQ, and against an Undertaker victory. In the words of Eric Bischoff - “controversy creates cash”, and with this match, you certainly get that.