Missed Opportunities: Top 15 Undertaker Matches The WWE Should Have Done

It’s hard to believe The Undertaker’s career is really over. We don’t say that because we think he’s going to come back, but rather because it was beginning to feel like The Undertaker was just going to have a match at WrestleMania until he physically couldn’t make his trademark entrance. The idea of Undertaker actually not being in WWE just seemed like an impossibility. Now, though, it seems that that Taker is truly finished. Now that his iconic career is behind him, we have plenty of time to look back on Taker’s greatest accomplishments as well as some of our own biggest regrets as fans.

Yes, while Taker may have faced many opponents during his storied WWE tenure, there is still a long list of matches that never happened. Now, it looks like those matches never will. In many ways, realizing that we’ll never get to see these matches makes The Undertaker’s retirement feel that much more real. Granted, some of these dream matches would require you to turn the clock back 20 or more years, but others were matches that could have theoretically happened if things had gone a little differently. Regardless, these are the top 15 Undertaker matches the WWE should have done.

15 The Undertaker vs. Eddie Guerrero

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For reasons we’ll never quite understand, The Undertaker and Eddie Guerrero never had a televised one-on-one match. That’s a mind-boggling fact that becomes all the more difficult to process when you realize these two were not only main event stars in their in-ring prime at the same time, but they were even both on the SmackDown brand for quite some time. We did get to see Eddie Guerrero and The Undertaker face off as part of a multi-man match at Armageddon 2004, but the brief interactions between the impossibly clever Eddie Guerrero and the always intimidating Undertaker made us crave a singles match between these two even more. It’s hard to say exactly when this should have happened, but it feels like the two could have had a number one contender match in 2004 either on SmackDown or on PPV.

14 The Undertaker vs. Scott Steiner

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This is an admittedly awkward match-up. There was never really any reason for these two to face-off during Steiner’s initial WWE run given that Steiner was barely in the WWE during that time and was rarely involved in anything but a tag match. However, a match between The Undertaker and “Big Poppa Pump” Scott Steiner would have been incredible. These two loved to have non-flashy, hard-hitting matches and would have surely found a way to turn in something memorable if they had the chance to do so.

These two never really crossed paths much during Steiner’s late WWE run, but WWE could have booked them in some kind of inter-brand match if they really wanted to during 2002-2004. Unfortunately, this was just another one of those instances of WWE not knowing what to do with WCW talent.

13 The Undertaker vs. The Ultimate Warrior (SummerSlam 1991)

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Here’s a strange one for you. The Undertaker actually did feud with The Ultimate Warrior in 1991. The two had a series of matches on the house show circuit (including a memorable body bag match at Madison Square Garden) but never really got a proper PPV match. In fact, Jake Roberts was inserted to the feud and bean battling with The Ultimate Warrior before Warrior and Taker could ever really settle their rivalry. The whole thing fell apart before many people were ever able to see these two settle what had been a great feud.

In retrospect, it feels like Warrior should have been pitted against The Undertaker at SummerSlam 1991 rather than have Warrior and Hogan team-up for a meaningless main event and for Undertaker to not be on the card at all.

12 The Undertaker vs. Umaga

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Given WWE’s fondness for having The Undertaker face off against every single “monster character” they can come up with, it’s a little surprising that The Undertaker and Umaga never had a proper match. There’s fan footage of these two facing off at house shows, but given how high WWE were on Umaga at the time - and how talented of a performer he was - it’s incredibly bizarre to consider that WWE never really let these guys work an extended program. Heck, Umaga against The Undertaker sure would have been a better 2006 feud than Taker against The Great Khali.

Undertaker and Umaga were only on the same show around the same time that Undertaker was had his great feud with Edge. However, WWE could have at least had Umaga be Vickie Guerrero's special enforcer hired to take out The Undertaker. Anything that would have gotten these two in front of a camera.

11 The Undertaker vs. Chris Benoit (SummerSlam 2003)

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These two had a few matches back in 2000, but there’s a pretty good reason you probably don’t remember them. The Undertaker was just figuring out his biker gimmick and Benoit was still trying to learn the WWE style. The two had good matches, but certainly didn’t put on the kind of all-time classic that we know they are capable of. After all, Chris Benoit could work with anyone and Undertaker was The Undertaker. As great as a WrestleMania showdown would between these two would have been, the only major PPV where these guy’s schedules didn’t conflict was SummerSlam 2003.

The Undertaker faced off against A-Train and Chris Benoit was involved in a forgettable Fatal 4-Way. Call us crazy, but Undertaker/Benoit seems like the better overall draw.

10 The Undertaker vs. Seth Rollins

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There are quite a few modern day stars who The Undertaker never got to work with. That’s what happens when WWE decides to book Undertaker once or twice a year and put him in a series of increasingly stale matches against Brock Lesnar. Bitterness aside, Seth Rollins is one of those modern stars who really should have gotten a match against Taker at some point. He’s actually the only member of The Shield to get a singles match against The Undertaker. Dean Ambrose faced Taker on SmackDown and Roman Reigns...well, you probably already know about Roman Reigns. You can argue whether or not Seth is the most talented overall member of the former group, but he does work the same in-ring style that some of The Undertaker’s best opponents used.

9 The Undertaker vs. Andre The Giant

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Andre The Giant and The Undertaker may not be the two best wrestlers in the history of WWE, but they’re certainly the most mythical performers in the history of the company. Andre and Taker are treated like gods by WWE and with good reason. Unfortunately, Andre and Taker never really got the chance to share the ring. To be fair, the timing on this one was incredibly awkward. By the time that Taker joined the company, Andre was barely able to walk much less wrestle a match. There was a time when they were still both technically active, but it would have been very difficult to put these two in a match. Still, can you imagine how incredible it would have been for Andre and Taker to battle in their respective primes?

8 The Undertaker vs. Goldberg

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WWE never really seemed to know what they had in Goldberg at the time that the former WCW legend joined the company in 2003. They put him in a few high-profile matches, but never appreciated the kind of draw Goldberg could really be. Specifically, they never put him against The Undertaker. It’s a match that books itself, honestly. WCW’s most feared wrestlers vs. WWE’s most feared wrestler. Our best guess is that WWE had a very specific booking schedule in mind for Goldberg, and The Undertaker wasn’t on that schedule. In retrospect, the best option probably would have been to put Goldberg against The Undertaker at WrestleMania XX. Taker could have still returned to his undead gimmick (needs to draw power to beat Goldberg and so on), and WWE could have avoided the Lesnar/Goldberg WrestleMania XX debacle.

7 The Undertaker vs. Hulk Hogan (WrestleMania VIII)

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Looking back, The Undertaker actually had a pretty interesting rivalry with Hulk Hogan. He was one of the few monster wrestlers that challenged Hogan during this period that was booked to look just as strong as Hogan was. The two even traded PPV victories, even though Taker’s win was due to interference shenanigans. After Hogan got the second victory, the entire feud was pretty much written off. In retrospect, the right move would have been to have a tiebreaker match at WrestleMania VIII between Taker and Hogan. Instead, we got Hogan vs. Sid Justice in a forgettable main event and Undertaker vs. a very drunk/stoned Jake Roberts. It’s doubtful that Taker’s eventual WrestleMania streak would have survived a match with Hogan, but a WrestleMania showdown with Hulk would have certainly been a spectacle.

6 The Undertaker vs. AJ Styles

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There’s a few stories involving this match that never happened which are all unconfirmed, but interesting nonetheless. Some stories suggest that AJ Styles was going to be Undertaker’s WrestleMania 32 opponent, but that got changed when the Shane McMahon return was finalized. A more recent rumor states that Styles was going to defend his title against Taker at Royal Rumble 2017, but that the writer responsible for this angle was let go and the whole thing got dropped.

Whatever the story is, you can’t help but feel a little sad when you think about how great this match could have been. Taker wasn’t in his prime for his last few matches, but there’s no way that anyone in WWE could have gotten more out of him from a sheer in-ring perspective than AJ Styles would have.

5 The Undertaker vs. Finn Balor

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Along with AJ Styles, Finn Balor certainly has to be the most requested modern day Undertaker opponent. The story is too good to ignore. You’ve got “The Demon” Finn Balor vs. “The Deadman” The Undertaker. It’s a similar angle to the one that WWE ran when The Undertaker wrestled Bray Wyatt at WrestleMania, but this one benefits greatly from the fact that Balor is a slightly more versatile worker than Bray Wyatt and that the feud could be used to really sell the “Demon” character. These guys' dueling entrances alone would be worth it. Unfortunately, these two just never really had the chance to meet in the ring. Even if Balor hadn’t been injured, it’s likely that WWE wouldn’t have asked Undertaker to work an extra date.

4 The Undertaker vs. Macho Man Randy Savage (SummerSlam 1992)

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Honestly, the only reason that this isn’t higher on the list is because these two did technically have a few matches. Undertaker and Savage squared off in a series of house matches during the early ‘90s. None of these matches were ever aired, and the only reason we know about them is because of footage that survived some of the dark matches that these guys worked for TV shows. As you might suspect, Undertaker and Savage had some pretty great matches together. So why didn’t they ever get a proper televised match? It’s hard to say. What we do know is that Undertaker/Savage would have been a great match for the SummerSlam 1992 card which suffered slightly from an underwhelming Randy Savage/Ultimate Warrior co-main event. The Undertaker vs. Savage in front of one of the largest crowds in WWE history would have been perfect.

3 The Undertaker vs. Daniel Bryan

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This one hurts more than some of the other theoretical Undertaker matches vs. modern day stars on this list for a couple of reasons. Obviously, the pain has something to do with the fact that Bryan was forced to retire while he was still in his in-ring prime, but there were also reports that The Undertaker asked to face Daniel Bryan at one point. The rumor was that this match was going to happen sometime around WrestleMania XXX. It’s still not entirely clear what happened, but it seems that WWE’s creative team simply never found the story that would have gotten these two in the same ring come WrestleMania. Because of this, we missed out on what could have been the greatest match of either man’s career.

2 The Undertaker vs. Sting

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Sometimes, you actually have to remind yourself that this match never happened. When Sting finally joined WWE, everyone assumed he was brought in to face The Undertaker. Why wouldn’t they? Taker/Sting had been a dream match for decades. The fact that Sting was brought in around the time of WrestleMania 31 only seemed to verify that these two legends were going to finally have the WrestleMania showdown that fans had been dreaming about. That didn’t happen, though. Undertaker wrestled Bray Wyatt on that card and Sting wrestled Triple H.

So why did we never get Taker/Sting? Unfortunately, that’s probably going to be one of those questions that never properly gets answered. WWE probably felt that Taker should face a young guy like Wyatt, but you do have to feel a little sad that this match is never going to happen.

1 The Undertaker vs. John Cena (WrestleMania 33)

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How long have fans been speculating that Undertaker vs. Cena at WrestleMania was going to happen? Five years? Ten years? There are times when it feels like the answer is “forever.” While the appeal of Cena/Taker was easier to understand before the Undertaker’s WrestleMania streak was broken - the man who never seems to lose vs. the man who never loses at WrestleMania - fans would have loved to have seen two of WWEs icons face off one more time. Again, the reason that this never actually happened seems to have something to do with the fact that WWE preferred to use some of Taker’s last matches to help younger guys get some exposure. Well...young guys and Shane McMahon.

There were also reports suggesting the WWE wanted the Cena/Nikki Bella proposal to happen at WrestleMania to garner mainstream media attention.

Much like the Sting match, though, this match should have happened for the simple reason that nobody wants to look back and remember that it didn’t.

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