For the entirety of my time as a wrestling fan, the two constants at the top of my favourites list were always Shawn Michaels and The Undertaker. After WrestleMania 33, they are both now done for good, which is something that is kind of hard to process beyond face value.
Even years after HBK's retirement, there are still rumours now and again that he will come back to have matches against folks like AJ Styles and Samoa Joe, although none of them ever turn out to be true.
Nearly a week later after The Undertaker's retirement, the initial shock has worn off and amidst the waves of nostalgia flashbacks and memories of The Deadman's great career, I find myself looking at the current roster and lamenting about the feuds we'll never be able to see.
There is so much talent in WWE at the moment between Raw, SmackDown, the Cruiserweights and NXT that it's hard to swallow The Undertaker is done for good and no more storylines will revolve around his character, nor will we see any classic matches with foes he would have paired fantastically with.
As such, it seems only fitting to talk about what could have been by pointing out several wrestlers The Undertaker could have had an amazing match with, even though it will sadly never happen.
#1 Braun Strowman
This is one of the most obvious ones, isn't it?
The Undertaker spent a good portion of his career acting as the resident giant-killer in WWE, fighting opponents like Kamala, King Kong Bundy, Giant Gonzalez, Kane and The Great Khali. At the moment, there’s no greater giant than Braun Strowman, as the guy is not just the most physically imposing, but even has the proper nicknames to go along with it.
“The Monster Among Men” and “A Mountain of a Man” are exactly the type of things we would have heard in the past about the people who temporarily made The Deadman seem weak until he would rise up against the challenge and put them down, usually at WrestleMania.
Strowman still has a lot to learn, but working with The Undertaker would have helped advance him further in his career much more in such a short amount of time, and The Phenom would have easily been trusted to carry him through any rough patches of their matches together.
#2 Samoa Joe
Keeping in line with the giant-killer aspect, WWE’s resident hitman Samoa Joe isn’t in need of the same type of treatment as Braun Strowman, as he’s a veteran in the business by this point, but he still could use a bit more legitimacy.
Over time, Joe will have his feuds with Roman Reigns, Seth Rollins, Dean Ambrose, John Cena and others, so his future shouldn’t be problematic in reaching that goal, but it would have been cool to see his style mesh with The Undertaker’s.
In particular, the past 10 years have seen The Undertaker adapt a more MMA-based approach to his in-ring work, which could have been fantastic to watch against Joe’s style.
If only Joe had moved from TNA to WWE a few years sooner, this would have definitely been on the table at some point, similar to the situation with Sting that is sadly out of the realm of possibility even if The Undertaker were still able to go.
#3 Finn Balor
It’s unquestionable that The Undertaker has had one of the best gimmicks in the history of professional wrestling, allowing him to go off the beaten track once in a while to have more obscure feuds that in any other scenario would have felt ridiculous.
Also read: Undertaker's retirement opens the door for Finn Balor
The Phenom fought an executioner, his severely burned hellion brother, a deranged psychopath who rips out his own hair, some kind of yeti creature and of course, the current roster’s resident southern cult leader.
Naturally, somewhere down the line, it would have been nice to see The Phenom go one on one with The Demon, even if the extent of Finn Balor’s gimmick ends after the bell rings as he doesn’t portray a character outside of “himself dressed up weird.”
Still, Balor is more than capable in the ring and the entrances alone would be a sight to behold.
#4 Dean Ambrose
One of The Undertaker's strengths was finding a way to brawl with the best of them, which is why so many of his matches were No Disqualification stipulations in some fashion. The Undertaker is responsible for birthing the Hell in a Cell, Casket Match, Buried Alive Match, Inferno Match and so forth throughout his career.
Just the same, Dean Ambrose is a madman who is always at his most entertaining when there are weapons involved, even going so far as to have the first-ever Asylum Match.
Had The Undertaker been in better shape during the past few years, there’s no doubt whatsoever that he and Ambrose would have crossed paths and settled their differences in some kind of insane hardcore match where they beat the hell out of each other.
#5 Seth Rollins
While on the topic of Dean Ambrose and having seen Roman Reigns already get his shot, it’s worth noting the other member of The Shield, Seth Rollins. The style of this match would have been drastically different from what we saw with Reigns or what could have been the scenario with Ambrose, as Rollins is much more of a technical wrestler.
Essentially, think of this as being more along the lines of The Undertaker’s matches with CM Punk.
Admittedly, there could have been a lack of chemistry between the two, but it would have been worth seeing if not just for one match to find out if they could strike gold in the process, as The Deadman was no stranger to the more subtle nuances of the ring rather than being someone who could only brawl.
Rollins, of course, would have to be the heel in this situation, so the timing wouldn’t be right for this current climate, but when he was with The Authority, that could have worked perfectly.
#6 AJ Styles
Perhaps the greatest wrestling match of all time was The Undertaker vs. Shawn Michaels from WrestleMania XXV.
If that’s the case, why would you ever want to deny fans the opportunity of seeing The Undertaker go up against the man most people equate to being the current torch-bearer of “best in-ring performer” in AJ Styles?
Again, this is a match that would have definitely happened if Styles had made the jump over to WWE just a little bit sooner than he did, as this was even a rumoured match for this year’s Royal Rumble.
This doesn’t have the same type of mystique the match with Sting would have had, but it’s definitely another pairing of legends that would have produced one hell of a match and it is unfortunate it will never come to pass. Also, who wouldn’t love the word-play of The Phenom against The Phenomenal One?
#7 Kevin Owens
If the rumours are true, Kevin Owens has been pitching working with The Undertaker for a long while, and given the circumstances, you can imagine why. Who wouldn’t want to have a feud with him?
Sadly, Owens was relegated to being another cog in the wheel of the Intercontinental Championship ladder match last year while The Undertaker was busy with Shane McMahon. Given the circumstances of the outcome, it can be argued that those plans should have changed.
This year, Owens had a great feud with Chris Jericho that needed to be wrapped up, plus WWE obviously wanted Roman Reigns to be the one to do the deed by putting The Undertaker down, so it wouldn’t have happened anyway.
This is purely a situation of bad timing which robs us of what could have been one of those dark horse feuds that seem odd on paper, but surprises everybody by being one of the best of the year, particularly given how Owens turns most of what he touches into gold.
The promos Owens would cut on The Phenom would be worth the price of admission alone.
#8 Sheamus
As someone who has never been the biggest Sheamus fan, it’s strange for me to admit this, but I’ve been calling for The Celtic Warrior and The Deadman to lock up for years. In my mind, it made no sense to do two years of Shawn Michaels matches followed by two years of Triple H, who had already wrestled The Undertaker at WrestleMania in 2001.
During the 2011-2012 time frame where Triple H took up two of those WrestleMania matches, Sheamus wrestled Daniel Bryan in a dark match one year and then in an 18-second match the next.
Mind you, this was also around the time he was still a main event talent who had accomplished many things, so he wasn’t some fresh to the scene jobber working his way up the ranks.
Sacrificing one of those Triple H matches for someone like Sheamus and giving us a full-on Celtic Warrior entrance against the dark wizard Deadman would have been a spectacle that launched Sheamus into the stratosphere.
#9 The Miz
Talk about a guilty pleasure. Imagine how insane a feud between The Miz and The Undertaker would have been!
As far as the in-ring aspect of this, don’t get me wrong—I’d much rather see Dolph Ziggler against The Undertaker, or even possibly Baron Corbin could have better chemistry with him. But when it comes to character work, there may be nobody in the company who knows how to work their gimmicks better than The Undertaker and The Miz.
The promos would be out of this world, both in comedic resonance and at times, pure intensity. This would be a squash in so many senses, as there’s no way The Miz would stand a chance when booked against The Undertaker, but that in itself could be immensely fun to watch.
#10 John Cena
Rounding out the list is the match everybody thought was coming our way last year, and if John Cena wouldn't have been injured at the time, it most likely would have happened. Despite everything that has happened over the past decade, there is still only one top dog in WWE and his name is John Cena.
Considering The Undertaker’s status as not only a legend, but also a locker room leader, seeing him go toe-to-toe with John Cena would have been only natural. Of course, it wouldn’t be a passing of the torch situation as The Undertaker had already given Cena an endorsement in his early days.
Instead, it would be a case of the two rightful peaks of the company, clashing to determine who has the slight edge over the other.
In a scenario where The Streak was still alive, this would have been the absolute biggest match the company could have produced, and nothing would hold a candle to it unless WWE could figure out a way to bring Andre the Giant back from the dead.
Fans who wanted to see this will have to settle for Roman Reigns taking that spot instead, which is just one more reason a lot of folks complain about the Reigns/Cena treatment. Are there any stars you would have liked the Undertaker to feud but can’t because of his retirement? Tell us your ideas in the comments below!
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