The Undertaker will forever be known as one of the most legendary superstars in WWE history. Not only has the Hall of Famer been a prominent figure in WWE programming for an unprecedented 30 years, but his ability to have matches with various superstars showed just how talented and versatile “The Deadman” really is.
Throughout 1990s, The Phenom had some of his best WWE matches against smaller opponents including Bret Hart and Shawn Michaels. However, he also competed against larger superstars like Giant Gonzalez and Mabel.
As the years went on, The Deadman continued to face superstars of all sizes and abilities – from Kurt Angle and Rey Mysterio to Brock Lesnar and The Big Show – and he occasionally recommended possible opponents who he could go head-to-head with in the future.
In this article, let’s take a look at five WWE Superstars who The Undertaker requested to work with, as well as four who he did not request to work with.
#9 The Undertaker requested to work with AJ Styles
The Undertaker's last match took place at WrestleMania 36. The event itself was unique, with it being the first edition of WWE's flagship event to have no fans due to the global pandemic. While the entire pay-per-view took place inside the WWE Performance Center, The Phenom took AJ Styles to the limit in a Boneyard match.
The Boneyard match was a cinematic version of WWE's Buried Alive gimmick match, which saw The Undertaker summoning 'The Unholy Trinity' to fight Styles. Later, the WWE Hall of Famer revealed that he was retired, making this match his final one for the company.
Reports revealed that The Prince of Darkness handpicked The Phenomenal One as his opponent because he felt that Styles is the modern-day Shawn Michaels.
#8 The Undertaker did not request to work with Sting
The never-before-seen dream match between The Undertaker and Sting has been speculated about for over two decades, so why has it never happened? Well, according to a 2017 interview that Sting gave to Al Arabiya English, the WCW legend spoke to The Prince of Darkness about a possible match, but his enthusiasm to face the WWE Superstar “wasn’t necessarily reciprocated”.
The Undertaker elaborated on the constant Sting rumors three years later, which returned after his Boneyard match against AJ Styles. He explained to Comic Book that it would be difficult for the two veterans to appease WWE fans in a match that has been hyped up so much.
“There’s so many people that are clamoring for that match that I just don’t know that the match could deliver on the people’s expectations. And the only reason I say that, I’ll take full [responsibility], I don’t have the mobility or the same skill set that I once did that I would need to make that match great.”
The Phenom also used the phrase “never say never” in the interview, but it seems unlikely that "Taker v/s Sting" will ever happen.
#7 Requested to work with: Triple H
The Undertaker’s back-to-back matches against Triple H at WrestleMania 27 and WrestleMania 28 are among the most memorable of both superstars’ careers, but their first high-profile match at WrestleMania 17 is also an underrated classic.
In the months leading up to the event, The Phenom was primarily involved in tag team storylines with Kane, while Triple H’s feuds with Kurt Angle and Steve Austin ended.
Triple H told the New York Post that both men spoke backstage about their lack of direction for WrestleMania 17 and they requested Vince McMahon to go one-on-one at WWE’s biggest show of the year.
“One day Mark [Calaway] and I just happened to be talking and I’m like, ‘What are you doing for ‘Mania?’ And he was like, ‘Man, I got nothing. They were supposed to do this, it fell apart. I was supposed to do that, it fell apart.’ We were in the same boat and the two of us at like the same time we’re like, ‘Ah, hey, you want to work ‘Mania?’”
Now that he has to deal with creative decisions in NXT and WWE, Triple H said he understands how both he and The Undertaker were almost left off the WrestleMania card. However they had chips on their shoulders at the time and wanted to steal the show.
#6 Did not request to work with: Goldberg
The Undertaker’s match against Goldberg at WWE Super ShowDown 2019 will go down in history for all the wrong reasons. On paper, the first-time-ever encounter seemed like a great idea. In reality, however, Goldberg legitimately knocked himself out early on in the match, meaning the rest of the nine-minute main event was full of uncoordinated moves and unfortunate mistakes.
Speaking on the fourth episode of the WWE Network series, "Undertaker: The Last Ride", Taker said he received a call from Triple H about WWE’s plans for him to face Goldberg in Saudi Arabia.
"It was Triple H that called me and asked me, 'What do you think about working with Goldberg in Saudi?' And I said, 'Wow, I mean, on paper, that's huge.' And I never worked with him. At this juncture in my career, you don't have very many opportunities to work with somebody of that magnitude for the first time ever kind of deal." [H/T Wrestling Inc.]
The Phenom added that he was “pretty excited” for the contest and he hoped that he and Goldberg would be able to live up to the hype.
As it turned out, The Undertaker left Saudi Arabia questioning whether he should retire as an in-ring competitor after a botched Jackhammer almost caused him to severe a serious neck injury.
#5 Requested to work with: Ric Flair
The first episode of "Undertaker: The Last Ride" primarily focused on The Phenom’s attempt to restore confidence in himself after he suffered a concussion against Brock Lesnar at WrestleMania 30. Although WWE fans will remember the match forever, The Undertaker’s injury was so severe that he could not recall anything that happened during the 25-minute encounter.
Footage from WrestleMania 31 showed Taker looking concerned as he waited anxiously backstage before his return match against Bray Wyatt. Triple H even went over to the WWE legend and convinced him he had nothing to worry about, much like he did over a decade earlier with Ric Flair.
At WrestleMania 18 in 2002, Flair was a 53-year-old veteran who lost confidence in his own in-ring ability after a difficult few years in WCW. So, despite his own lack of self-belief, he was offered the opportunity to face The Undertaker.
"When I was at the worst possible point of self-confidence, [Triple H] came to me and said, ‘Taker wants to work with you at [WrestleMania] 18.’ I said, ‘Taker does?’ I couldn’t believe it." [H/T Fightful, via Broken Skull Sessions]
Flair lost an 18-minute match to The Undertaker and continued to compete in WWE for another six years.
#4 Did not request to work with: Mabel
One of the worst injuries of The Undertaker’s WWE career came in 1995 when he sustained a broken orbital socket after receiving a botched leg drop from Mabel (aka Viscera/Big Daddy V).
Speaking on NotSam Wrestling, the WWE Hall of Famer was asked about his dependability as an in-ring performer and Vince McMahon’s decision to have him face “eight-foot guys (Giant Gonzalez)” and “a six-hundred-pound man (Mabel) who dropped his leg on your face”.
The Phenom responded by saying he frequently asked McMahon if he could face more trusted superstars instead of large rookies who could potentially hurt him.
"I begged him [Vince McMahon] all the time. It was funny because I knew somebody would come in and I would know, even before I got the call into his office, I knew he's heading my way."
The Undertaker’s injury was so bad that he had to wear a mask for the rest of his rivalry with Mabel, which culminated in “The Deadman” winning a casket match at In Your House 5: Season’s Beatings in December 1995.
#3 Requested to work with: Yokozuna
Conversations about the greatest big men in WWE history usually revolve around the likes of Andre The Giant and The Undertaker. Still, nobody can deny that Yokozuna deserves to be on that list of names.
The Hall of Famer debuted in WWE in October 1992 and immediately established himself as one of the top superstars in the company, winning the 1993 Royal Rumble before headlining WrestleMania 9 against Bret Hart – and then Hulk Hogan – just six months after his first televised appearance.
In the penultimate match on the WrestleMania 9 card, The Undertaker was in action against Giant Gonzalez. Speaking on NotSam Wrestling, The Undertaker revealed in 2020 that he asked Vince McMahon if he could work with Yokozuna before feuding with the less talented Gonzalez.
“He [Yokozuna] was doing a dark match in Baltimore, so I see Vince standing there watching him, and me and him are both watching him and the stuff that he's doing and the kicks he's throwing at four-hundred pounds. I remember turning my head to Vince and saying, 'Please, please, please, let me work with him first.'” [H/T Wrestling Inc.]
Taker and Yokozuna faced each other at dozens of live events in 1993, but their only major televised feud came in 1994 when they went one-on-one in casket matches at the Royal Rumble and Survivor Series.
#2 Did not request to work with: Giant Gonzalez
The Undertaker’s conversation on NotSam Wrestling about the Yokozuna/Giant Gonzalez situation did not end there. Mark Calaway, the man behind the character, has spoken very positively about the majority of his WWE opponents since he began giving media interviews to promote his "Undertaker: The Last Ride" series on the WWE Network.
However, when it comes to Giant Gonzalez, The Undertaker has given his brutally honest opinion on working with the towering Superstar. Continuing to reveal what was said in his backstage conversation with Vince McMahon, the WrestleMania icon recalled that Giant Gonzalez walked down the hallway mere seconds after he said he wanted to face Yokozuna.
“[Vince McMahon said] 'You'll work with him [Yokozuna] in time, but I've got somebody else in mind for you.' I kid you not, coming down the hall from the other direction, here comes Giant Gonzalez, and Vince goes, 'That's your guy.'” [H/T Wrestling Inc.]
The Phenom added that his battles with Giant Gonzalez, which spanned 29 matches (including live events) from March 1993 to SummerSlam in August 1993, “took years off my career”.
#1 Requested to work with: Drew McIntyre
Another notable comment from "Undertaker: The Last Ride" came when The Undertaker revealed that he had already agreed to compete at the WWE Extreme Rules pay-per-view in July 2019 before he fought Goldberg five weeks earlier at Super ShowDown.
Following the disappointing Goldberg vs. The Undertaker match, it had been widely speculated that both Superstars made quick returns to WWE television in an attempt to redeem themselves for what happened in Saudi Arabia. Still, Taker clarified that his Extreme Rules booking was always on the cards.
“Sports Illustrated learned that McIntyre was on the short list of Undertaker’s requested opponents following his debacle in Saudi Arabia against Bill Goldberg at the Super ShowDown.”
The heavily rumored match between The Undertaker and McIntyre at SummerSlam 2019 did not come to fruition. Still, The Phenom did team up with Roman Reigns to defeat McIntyre and Shane McMahon in a No Holds Barred tag team match at Extreme Rules.
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