Since 1991, WrestleMania has been defined by The Undertaker and his annual battle on WWE’s grandest stage.
His matches with Shawn Michaels, Triple H, Brock Lesnar, Ric Flair and CM Punk have stolen many a show, enhanced the overall presentation of several incarnations of The Showcase of the Immortals and strengthened his considerable legacy.
One look at his legendary career suggests there were plenty of opportunities for even greater matches on the grand stage that, for whatever reason, went unrealized.
From monumental clashes with his greatest rival to a chance to bury Hulkamania at the show on which it ran wildest, they are battles that may well have altered the course of The Phenom’s career.
Now as he prepares to square off with Roman Reigns in one of the most prominent matches of WrestleMania 33, take a look at what may have been had The Deadman clashed with these epic opponents on the Grandest Stage of Them All.
The Undertaker vs. Bret “Hitman” Hart
The Undertaker and Bret Hart helped define WWE in the 1990s. They battled countless times, including matches at the 1996 Royal Rumble and 1997 SummerSlam, yet never came together for the epic WrestleMania bout they both probably deserved.
Two of the elite stars for Vince McMahon’s company during a period of time where the boss was not worth a billion dollars and the company could not sell out 100,000-seat stadiums, they remained loyal to the promotion.
Yet, despite being at the top of their games for as long as they were, their paths never crossed in time for a WrestleMania showdown.
Part of that can be credited to the fact that they were never in position to square off with each other. At the height of their careers, they were both babyfaces at a time when good guys simply did not wrestle other good guys.
Thus, it was essentially an impossibility they would compete against each other on wrestling’s most important night.
As it stands now, their best televised match came in September 1997 at WWE’s One Night Only pay-per-view.
The Undertaker vs. Chris Jericho
Undertaker and Chris Jericho have been in the same company since 1999 but have worked with each other only a handful of times. None of them has been at WrestleMania, a stage both men have left their mark in over the course of their Hall of Fame careers.
The most perfect opportunity for the match to occur was in 2010.
At that year’s Elimination Chamber pay-per-view, Jericho controversially defeated Undertaker for the World Heavyweight Championship. It would have been easy to have The Deadman avenge his loss and regain his title at the event.
Except, you know, that whole epic storyline he was in the middle of with Shawn Michaels.
One year after he defeated The Heartbreak Kid at WrestleMania XXV, Undertaker was faced with a pit bull-like tenacity by Michaels, who would not rest until he had the opportunity to try one last time to defeat The Phenom on the grand stage.
There was no room for Jericho, who was in the midst of his own story, and the most significant opportunity to bring Y2J and Undertaker together on wrestling’s biggest night passed WWE by.
The Undertaker vs. Hulk Hogan
The Undertaker and Hulk Hogan have waged war under important circumstances, the most memorable being the marquee match of the Survivor Series pay-per-view. They have beaten each other and earned championships along the way.
Despite being in WWE at the same time between 1990-93, then again in 2002-03, the iconic Superstars never battled on the industry’s grandest stage.
There was certainly opportunity, perhaps none better than WrestleMania XIX.
Imagine a scenario where Vince McMahon, eager to end Hulkamania once and for all, reached out to his greatest creation, Undertaker, and recruited him for the task. Sure, it would have been out of character for The American Badass, but it would hardly have been the first time he turned heel suddenly and unexpectedly.
Given Undertaker’s systematic destruction of Hogan just months earlier at the Judgment Day 2002 pay-per-view, it would have made sense for McMahon to convince The Phenom to add the biggest star in the history of professional wrestling to his graveyard of WrestleMania victims.
As it stands, that never happened, and WWE missed out on the opportunity to book a match between the man who built the event and the Superstar who defined it.
The Undertaker vs. Mankind
Perhaps no rival of Undertaker’s was greater than Mankind, a twisted and psychotic villain whose willingness to sacrifice his body for the sake of crippling his opponents made him the perfect foil for The Deadman. Even more useful was his mastery of mind games.
For so long, Undertaker had been able to intimidate his opponents through mind games. When Mankind came along, he was forced to reinvent himself. He became darker and more physical, throwing rights and lefts rather than the robotic thrusts to the throat that had previously defined his striking game.
He embraced a more brawling style that fans of his today are familiar with.
Their rivalry in 1996 did as much to prepare fans for the impending Attitude Era as anything, introducing a wild and chaotic style unlike any the audience had ever seen before.
Unfortunately, it wrapped up before WrestleMania 13 in the spring of 1997.
Had management been willing to run with the feud just a few more months, Mankind could have won the WWE Championship, setting up an epic war with his greatest rival over the top prize in sports entertainment.
It would have made for a more suitable conclusion to the first chapter of their feud, a better match than Undertaker vs. Sid proved to be and given that event the very real chance at another extraordinary battle to go along with Bret Hart vs. Steve Austin’s Submission match.
The Undertaker vs. Kurt Angle
In a 2015 interview with Raj Giri of WrestlingInc.com, Kurt Angle revealed Undertaker once suggested losing his undefeated streak to the Olympian.
“I was champion in 2006 and Undertaker approached me and said he wanted to face me at WrestleMania. Until then, Undertaker didn’t have a WrestleMania moment with a five-star match. He thought he could have that with me, and he was considering possibly losing as long as he had that moment he wanted, and I don’t blame him. Vince said no way, and I agreed with Vince. I don’t think Undertaker should ever have lost at WrestleMania, I think he should have been undefeated forever.”
Instead, they had a phenomenal match at No Way Out, one month before The Showcase of the Immortals.
Throughout their run in WWE, Undertaker and Angle repeatedly demonstrated an ability to steal the show with fantastic matches and entertaining vignettes.
If that match from No Way Out had taken place at WrestleMania, instead of The Phenom’s nondescript Casket match against Mark Henry, he would have strengthened an already all-time great resume with what was a legitimate match-of-the-year candidate.
Instead, he competed in one of the more forgettable matches of his streak.
The Undertaker vs. “Stone Cold” Steve Austin
The Undertaker and “Stone Cold” Steve Austin had an ungodly number of matches with each other over the course of their careers. From a Monday Night Raw match early in Austin’s tenure to the main event of SummerSlam 1998 inside Madison Square Garden, it felt like every few months the future Hall of Famers locked horns in some high-profile bout.
For all of the wars they waged and all of the matches they wrestled, The Texas Rattlesnake and The Phenom never did battle at WrestleMania.
The year 2002 would have been an opportune time for it to happen. Undertaker was in the midst of a major heel run, and Austin was clearly unmotivated by working with the New World Order.
While The Deadman’s feud with Ric Flair resulted in some heated moments and a good, bloody brawl on the grand stage, bringing Undertaker and Austin together to have that same type of match would have meant more to both of their careers.
Austin, who accomplished everything else there was to do, could have crossed “wrestle Undertaker at WrestleMania” off the ol’ bucket list while The Phenom could have etched another icon’s name on a tombstone.
Alas, the longtime rivals never did mix it up at The Showcase of the Immortals, but thankfully, fans have their numerous other matches to remember and relive fondly.
The Undertaker vs. John Cena
When all is said and done, the biggest missed opportunity in Undertaker’s superb WrestleMania legacy will be the lack of a one-on-one match with John Cena.
“What if?” is a question fans will ask for decades as their appetite for a battle between the iconic Superstars on The Grandest Stage of Them All goes unfulfilled.
Cena, the biggest star of his generation and one of the most prominent in company history, has battled every major competitor of his era but never stood across the squared circle from The Phenom on the stage he elevated to such prestige.
There have been opportunities for the match to occur.
In fact, never has the opportunity better presented itself for the epic showdown between industry Superstars than in 2017. Both represented SmackDown Live initially. Despite the absence of an overly complicated storyline, the feud sold itself: the two most recognizable stars in the company, dominant in their fields, clash to determine who the best is once and for all on WWE’s most spectacular night.
Unfortunately, Creative opted to take both stars in opposite directions.
Undertaker moved to Raw to face Roman Reigns, while Cena uncharacteristically settled for a spot in the midcard, teaming with girlfriend Nikki Bella to battle The Miz and Maryse in a Mixed Tag Team match.
It is an unfortunate situation given how lucrative the match could be for WWE, how iconic it could be for fans and how definitive it could be for the men involved.