6 WWE Superstars we desperately wish The Undertaker would have faced before he retired

If you've followed the WWE Network Documentary Undertaker: The Last Ride, the fifth and final part seemed to indicate that WrestleMania 36 was, in fact, The Undertaker's last ride. Over the course of the documentary, we saw multiple glimpses of the aging legend and his body taking a toll on him.

"I have this other life that I need to go experience and enjoy the fruits of my labor."#TheLastRide @undertaker pic.twitter.com/THpD5TkbVa

— WWE (@WWE) June 22, 2020

One such example was a backstage clip from Extreme Rules 2019, where he teamed up with Roman Reigns to face Drew McIntyre and Shane McMahon. While that was his best match in years at the time, he went backstage post-match and told Vince McMahon that he was "done" and that his body wasn't feeling it anymore.

He eventually did come back in a big way and if The Boneyard match against AJ Styles was the end of his run, then we couldn't think of a more appropriate opponent or way to go out. Styles tweeted out in respect of The Phenom himself, saying:

Still floored by the experience and reaction to the #BoneyardMatch at #WrestleMania.If it was the last time @undertaker laced up his boots, I’m honored it was against me. #TheLastRide https://t.co/qzofoKEn2Q

— AJStyles.Org (@AJStylesOrg) June 21, 2020

With all the legendary names that The Undertaker has faced, there are a few who we wish he interacted with but never got to. Let's start with one of the biggest legends in WWE history.

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#6 'Macho Man' Randy Savage against The Undertaker

The two only got to square off on the live event circuit

We must mention now that this list specifically refers to televised matches. In this case, The Undertaker and 'Macho Man' Randy Savage did have a series of matches - but they were untelevised live events in the summer of 1991.

The Undertaker was supposed to be working with The Ultimate Warrior, who couldn't appear for a set of shows. Randy Savage would beat The Undertaker multiple times, but it's a shame that we never got to see them face off on TV.

'Macho Man' Randy Savage was directly involved in The Undertaker's face turn in early 1992 as he stopped his ally Jake 'The Snake' Roberts from a sneak attack on Savage and his wife Miss Elizabeth.

Savage was the catalyst for Undertaker's face turn and it's a shame that they never got to have a proper feud. While The Undertaker turned out fine anyway, we can't help but wonder what Randy Savage's run in WWE would have been like post-1993 if he was able to work with young superstars at the time like The Undertaker and Shawn Michaels.

It's one of those fantasy matches that will remain just that - a fantasy match.

#5 Daniel Bryan

The Undertaker and Daniel Bryan have shared a ring but not on the opposite sides

This is a match that could have happened in 2013 while Daniel Bryan had momentum. While The Undertaker had been a babyface for a long time at that point, face vs face feuds wasn't exactly uncommon.

The two have shared a ring - but not on the opposite sides. In 2013, The Undertaker was ambushed by The Shield, who were still close to a year away from turning face and breaking out as singles stars. Daniel Bryan and Kane would make the save and it would lead to the three of them teaming up in a losing effort against The Shield.

One could argue that the timing was never right to have the feud, but a dream match between Daniel Bryan at his peak and The Undertaker would have sold well regardless of whether there would be a build-up or not. There's no doubt that Daniel Bryan could have given The Undertaker as good a match as CM Punk did at WrestleMania 29.

#4 Braun Strowman

The WWE Universal Champion

Braun Strowman was rumored to be The Undertaker's WrestleMania opponent in 2017 at one point. However, it was Roman Reigns who ended up taking that spot (becoming only the second man to beat The Undertaker at WrestleMania).

While there was little chance of Strowman ever beating The Undertaker, there's no doubt that at the time, he was extremely deserving of having that match. He was the hottest Superstar in WWE in early 2017 and his momentum even spilled onto 2018 despite suffering a couple of big losses to Roman Reigns early in 2017 and Brock Lesnar later in the year.

It would have been the perfect time to pull the trigger on him and elevate him, but the running theme of WWE's main event scene was their push of Roman Reigns, which involved compromising other wrestlers and their momentum.

Strowman essentially suffered the same fate as Jon Moxley/Dean Ambrose did in 2016, but it took him a few more years to become Universal Champion. Still, it's a shame that we never got to see this dream encounter between the two big men.

#3 Eddie Guerrero

The two never had a singles match

Wouldn't have this been a special match for The Undertaker? Eddie Guerrero and The Undertaker have shared a ring, but it was in a Fatal-4-Way match also involving then-WWE Champion JBL, and Booker T. Since JBL was having the run of his career, WWE felt that it would be best for his momentum to carry forward to the next year.

It was the final PPV of the year and Eddie Guerrero was a few months removed from his WWE Championship reign. While many considered it memorable, Guerrero took a look at the declining ratings while he was Champion and took it personally, requesting Vince McMahon to take the title off him.

They used the opportunity to establish a main eventer in JBL, who would go on to put over John Cena in the latter's first of 16 World championship wins at WrestleMania 21. Guerrero was indirectly a catalyst for Cena's rise, though we don't doubt that it would have happened anyway.

Eddie Guerrero vs The Undertaker would have been a match for the ages, especially if you consider the quality of talent and matches on SmackDown at the time. The two were having great runs.

#2 Drew McIntyre

We could only get a tease

This is perhaps the biggest dream match The Undertaker can have on the current roster now that he's faced AJ Styles. At Extreme Rules 2019 in their previously mentioned tag team match, The Undertaker would have a face-to-face confrontation with Drew McIntyre, teasing the possibility of a feud down the line.

Such face-offs aren't done without intention and had The Undertaker not retired, we do not doubt that WWE would have liked to book this match, likely with the intention of helping McIntyre in his run on the top.

The "new" Undertaker would have made for a great WWE title opponent, but either way, it's a match that we're never going to get. Drew McIntyre revealed that he was supposed to face The Undertaker at WrestleMania 26 when he was just 24 years old, but admitted that he wasn't ready at the time:

“When I was 24 I was told by Vince McMahon, ‘you don’t listen to anybody but the Undertaker, he’s going to be your mentor and whenever you’ve got a question you go straight to him’. And the inevitable goal was to have a big match between him and I. Unfortunately I wasn’t ready at the time, things worked out the way they worked out, and I believe it led to, instead of myself and Undertaker, Shawn Michaels and Undertaker, the retirement match. It was obviously a phenomenal match and I could not have delivered on that level at the time.”

McIntyre is right in believing that he wasn't ready. 2020, however, would have been a whole different story.

#1 Sting

Sting was a late arrival to WWE

We couldn't have ended this list without the former WCW superstar and for a short time, WWE superstar as well - Sting. The Vigilante perhaps ranks as The Undertaker's greatest dream opponent - a match that should have happened years ago but never came to pass.

Sting revealed to The Daily Star in 2011 that he was offered a match against The Undertaker at WrestleMania 27 along with a WWE Hall of Fame induction (H/T WrestlingInc):

"There are so many variables. Let's just say that I turned it down for the same reasons I always have. Something in me never trusted what would happen up there, based entirely on the track record with other WCW guys and everything that went on after Vince [McMahon] bought WCW."

It's not a surprise to see why Sting took so long to join WWE. However, Vince McMahon proclaimed that someday, they would do business together. Unfortunately, Sting's run in WWE was a bit disappointing as it only featured two major matches - a losing effort to Triple H on his WWE debut at WrestleMania 31 and a WWE title match against Seth Rollins at Night of Champions later that year in 2015 - a match that ended his career and took away the possibility of a bout with The Undertaker.

It's too late now with both Sting and The Undertaker retired and unfortunately, the dream match is going to remain a dream.