WWEis rich in lore, history, and iconic moments, but none have been more iconic thanThe Undertaker’s undefeated Streak at WrestleMania. Even when that Streak came to an end, his preceding WrestleMania matches were still considered must-see because of the legacy that the Deadman built at the Showcase of Immortals.
The names Undertaker and WrestleMania are synonymous with each other. Even now that Undertaker is some years removed from his last WrestleMania match and deep into his retirement, the event just does not feel the same without his presence at the Showcase of the Immortals. Not only was his Streak significant because of how lengthy it was (ending at 25-2), but because his matches would often be the best of the night - though not always.
27Undertaker vs. Giant Gonzalez
WrestleMania IX
This match stands out as the only asterisk and blemish on The Undertaker’s record. even bigger than his only two losses at WrestleMania, all becauseit’s the only match in his record where he won without pinning or submitting his opponent. Instead, as a result of the 8-foot-tall giant dosing The Deadman with a chloroform-soaked towel, The Undertaker won by disqualification.
It’s certainly a strange way to end any match at WrestleMania, let alone a Streak match, but truth be told, the DQ finish felt like a mercy kill, as the 8 minutes of the contest were some of the slowest, most prodding of Taker’s career. Undertaker’s matches with big men could be a mixed bag. They could either be a fun car crash featuring big meaty men slapping each other, or a car wreck featuring less-than-exciting action, and largely because of Gonzalez’s struggles with his body at the time, this fell into the latter.
WrestleMania XV
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There’s a reason whythis match is often hailed as the worst Hell in a Cell match of all time, and some of it doesn’t have anything to do with the match itself. For starters, the sight of The Undertaker’s post-match hanging of the Big Boss Man always made for uncomfortable viewing, even for the live crowd in attendance.
As for the match itself, there were too many elements that prevented this match from being something worth investing in. The chemistry wasn’t there, the brawl wasn’t captivating, and perhaps worst of all, the match pitted one heel against the other, not giving the audience anyone to reasonably cheer for. There was nothing here for viewers to do but to count down the seconds until it was all finally over.
25Undertaker vs. Shane McMahon - Hell in a Cell
WrestleMania 32
This might be one of the more confusingly booked matches in WrestleMania history. Going into it, everyone loved seeing Shane McMahon return, but the stipulation was had he won, he’d become the Raw General Manager and Undertaker would be forced to never wrestle at WrestleMania again.No one wanted to see the latter. Keep in mind that both men were babyfaces, making it all the more confusing.
What we got is an Undertaker past his prime and without a Streak to maintain interest in the match, and a Shane McMahon who added years of ring rust to his already not-so-fabulous wrestling skills. It’s a lose-lose for everyone involved. At least it has the predictable, but ever-excitingdive from the cageand a sequence of high-risk, high-impact spots where poor Shane put his body on the line for our entertainment.
24Undertaker vs. Roman Reigns - No Holds Barred
WrestleMania 33
There was a time when audiences believed thatRoman Reigns would make the perfect candidate to end the Streak. During his rookie days with the Shield, knowing he was a top prospect, it once made sense for him to be the one to beat Taker at WrestleMania. Those days had long passed by the time they wrestled at WrestleMania 33, a time when Roman was entering his third WrestleMania main event as a multi-time former WWE Champion.
He didn’t need to beat The Undertaker, and knowing audiences would see Roman face the man who did break the Streak in the following year’s WrestleMania,this win felt like a pointless way to feed Vince McMahon’s vanity projectin his hyper-fixation on pushing Roman Reigns. This match exists only to make Roman look strong when he already looked mighty strong. Booking complaints aside, the match is just filled with sloppy spots that made watchers feel as if it was time for Taker to finally hang up his boots.
23Undertaker vs. King Kong Bundy
WrestleMania XI
While he’s a name that doesn’t get brought up a lot in the grand scheme of WWE history, King Kong Bundy’s status as a legend is undeniable as one of Mania’s first main eventers, having headlined WrestleMania II in a Steel Cage match for the WWE Championship against Hulk Hogan. By WrestleMania XI, though, almost 10 years after the fact,Bundy is visibly past his prime against the Undertaker.
Again, big man bouts have always been a mixed bag for the Undertaker, but when he’s dealt an opponent who isn’t allowed to live up to his old-school reputation because of his age, that makes it all the harder to have a compelling match. It doesn’t help that the match is watered down further by shenanigans revolving around Ted Dibiase and the Million Dollar Corporation.
22The Undertaker vs. Big Show and A-Train
WrestleMania XIX
What’s most surprising is thatthis match was close to being worse than it ended up being, as it was originally scheduled as a tag team match that would have seen the founder of Deadman Inc. team with his pupil, Nathan Jones, to take on A-Train and Big Show. At the last possible minute, the admittedly green Jones was considered too green to wrestle on the biggest show of the year. During the night’s Sunday Night Heat pre-show, Jones would be attacked by the Full Blooded Italians - not his would-be Mania opponents, oddly enough - and thus, the match was made a Handicap Match.
On one hand, seeing Taker beat two men in one night did make for a better showcase on his Mania resume, while taking Jones out easily made for a better contest. On the other hand,“better"isn’t saying much. The only thing worse than Taker wrestling a big man that he doesn’t have chemistry with is seeing him wrestling two.
21The Undertaker vs. Sycho Sid - WWE Championship
WrestleMania 13
Undertaker’s first WrestleMania main event is more of a whimper than a bang, but it isn’t either his or Sid’s fault. The former WWE Champion (and hopefully future WWE Hall of Famer) and the main event’s eventual victor were both competent big men, but despite both men getting 21 minutes worth of time they shine,they couldn’t shine because they were being actively overshadowed.
First, they were overshadowed bythe earlier instant classic between Steve Austin and Bret Hart, which still stands tall asone of Stone Cold’s best matches, not to mention a star-making performance. That was always going to be hard to follow up. Then, the match is overshadowed by Shawn Michaels on commentary, and Bret Hart’s interference, along with their ensuing shenanigans. While neither Sid nor Taker do anything outright wrong in the match themselves, their match was set up to fail before it even began.
20The Undertaker vs. Kane
WrestleMania XX
Spoiler alert for later in the list, but Undertaker and Kane’s earlier contest from WrestleMania XIV ranks among one of the former’s best Mania matches, and one of the best matches in either man’s career. This match, though, failed to live up to that same kind of expectation simply because this match wasn’t set up to be the same kind of back-and-forth big man showcase it was more than half a decade beforehand.
This would markthe first time in years that Undertaker would come out as the Deadman characterafter first debuting the biker character in 2000. As a result, this served as more of a showcase of Taker’s reintroduction of that character rather than existing to showcase a match. The match is solid in setting up what it tries to achieve, at the cost of sacrificing the opportunity for having another great match.
19The Undertaker vs. Jimmy “Superfly” Snuka
WrestleMania VII
This is the match that set the stage for The Undertaker’s presence on the Grandest Stage of Them All.It’s the first match Undertaker ever had at WrestleMania, and as a match to set the tone for his Streak, it’s not bad. It’s not quite anything to write home about as it doesn’t stand out alongside the classics he would have in later years, but it is a solid start to what would become an iconic run.
In under five minutes, Undertaker vs. Snuka have what can be best described as a competent match-up. Taker looks good in his first outing and despite being past his prime, Snuka does his best to help highlight the strengths of the young up-and-comer. It’s a simple squash match that would carry more weight, meaning, and relevance in later years as the Streak would become more prominent.
18The Undertaker vs. Jake “The Snake” Roberts
WrestleMania VIII
Much like the year prior, this was an instance ofa veteran putting over the rookie on their way out the door, but Roberts had the luxury of still being in his prime as a storyteller. Speaking of, because of the well-documented storytelling skills of Jake Roberts and considering just how much these two characters complement each other, some would expect this to be a true classic in the making.
Unfortunately, while not a bad match, it’s disappointing as just a fine one. A simple seven-minute match that doesn’t go out of its way to compel or reinvent the wheel. One factor could be that this would be Roberts' final match before his WWE exit.Whether Roberts being unmotivated is what prevented the match from living up to its full potential, he still at least does what he can to deliver a decent contest with Taker.
