For 23 years, it was the most impressive record in wrestling. Over 21 matches, 18 opponents, and countless pints of spilled blood, The Undertaker was undefeated at WrestleMania, with most fans believing he would never lose at the event. It reached a point where the chance of actually beating The Undertaker at WrestleMania was regarded as an even greater honor than winning the WWE Championship, and it isn’t surprising that Brock Lesnar still brags about pulling the seemingly impossible feat off at the 30th version of the event.
Despite all that, the more attention you paid to the Streak, the less impressive and bombastic it actually was. Sure, there were some pretty great matches starting around the halfway point, but those first few were pretty dire. Quite frankly, well after The Undertaker reinvented himself as a worker and started wrestling classics on a regular basis, there were still a few duds on the Grandest Stage of Them All bad enough to cheapen the most famous legacy attached to the show. In the very least, the good definitely outweighed the bad, and most fans will accept a weak match here or there if they add to classics down the line. Keep reading to discover the 8 best and 7 worst matches of The Undertaker’s WrestleMania undefeated streak.
15 BEST: WrestleMania XIV – Kane
At once The Undertaker’s closest ally and archrival, his kayfabe brother Kane is either one of his best or worst opponents depending on your individual views about what constitutes sports entertainment. Splitting the difference and calling Kane the weakest of his great Mania opponents, a more balanced read on their two matches can acknowledge that for every area the matches excelled in storytelling, they strongly lacked in actual wrestling. Kane and Undertaker squared off at WrestleMania XIV and XX, and we’ve chosen the first of their encounters as the better of the two, yet there wasn’t much of a difference between them. Aside from Kane acting more frightened the second time around, and thus leading to a slightly easier Undertaker win, the action itself barely changed, in and of itself displaying the pairing’s major failing. On the other hand, Kane and the Undertaker are one of WWE’s greatest duos, and their spectacles can’t be forgotten or ignored.
14 WORST: WrestleMania 22 – Mark Henry
There’s definitely some appeal in a match between The Undertaker and the “World’s Strongest Man” Mark Henry. Throw in the fact it was the Phenom’s only casket match at WrestleMania, and one might even think WWE had all the makings for a classic on their hands. Unfortunately, the match came during the exceptionally long period where Henry still hadn’t found himself as a performer, and its not like WWE did much with the idea, either. Unlike some of the more involved wars on this list, Undertaker and Henry’s issue started barely a month before WrestleMania and was quite generic. Henry cost Undertaker a World Heavyweight Championship match against Kurt Angle, and then they stared at each other making angry looks for a while. There just wasn’t much there, and the match itself followed in suit, featuring mostly punches and kicks with the casket barely involved.
13 BEST: WrestleMania X-7 – Triple H
Having ventured to the dark side at three separate WrestleMania’s, Triple H is The Undertaker’s most frequent rival at the event. Oddly, their first encounter was a fairly low-key affair, although their names alone were more than enough to make it the semi-main event at the greatest WrestleMania in history. Triple H was cheesed he didn’t get a WWE Championship shot despite beating Steve Austin and everyone else, so Undertaker pointed out Triple H never beat him, and that was all it took. Regardless of how simple it all seemed, the two confirmed they deserved their spot by putting on a wild 18-minute brawl throughout the crowd (also featuring one of the longest referee bumps we’re aware of). On the downside, the match was overshadowed by no less than two, maybe three other sheer classics on this list, not to mention the fact Undertaker and Triple H themselves would go on to top it in later years.
12 WORST: WrestleMania 13 – Sid
Sometimes in wrestling the greatest highs and deepest lows happen all at once. The Undertaker’s performance at WrestleMania 13 was integral to his career in that it was his first main event at the Showcase of Immortals, and also the start of his second WWE Championship reign. As important as both of those distinctions are, they don’t change the facts that both the build towards his encounter with Psycho Sid and the match itself were both ploddingly boring. Undertaker barely even did anything to earn the biggest title shot of the year, implausibly getting the shot by losing the previous month’s main event at In Your House: Final Four. When it came time for the two behemoths to do battle, they did as behemoths do, and mostly stared at one another imposingly while the real focus was Shawn Michaels sniping at Bret Hart from the commentary desk. Needless to say, the result was underwhelming, and Taker’s run with the title started with a whimper.
11 BEST: WrestleMania 29 – CM Punk
All things must come to an end, and if nothing else, the final victory of the Streak saw the concept go out with a bang. Undertaker and CM Punk were no strangers to one another, having feuded throughout 2009 over the World Heavyweight Championship. While it looked like that feud ended when The Undertaker bested Punk for the Big Gold Belt, things had changed considerably over the next four years thanks to Punk setting a new record as the longest reigning WWE Champion of the modern era. On the downside, instead of focusing on Punk’s increased credibility, WWE hyped the match around his equally heightened jerk behavior, mocking the actual death of Paul Bearer to get into the Dead Man’s head. Questionable build notwithstanding, their showdown delivered in spades, with many fans calling Undertaker going 21-0 the best match of the night.
10 WORST: WrestleMania VII – Jimmy Snuka
And so it begins. Four months into his WWE career, The Undertaker made an important albeit lackluster WrestleMania debut by defeating future WWE Hall of Famer Jimmy “Superfly” Snuka in less than five minutes. The feud between the two was pretty minimal, although that was simply the style at the time. Less forgivable was that Undertaker had already defeated Snuka pretty definitively on the house show circuit, including a televised match at Madison Square Garden. Maybe it would have worked had Snuka and Undertaker built on their previous matches at all, but instead what fans got was an out-and-out squash, the Superfly getting virtually no offense until a failed crossbody lead to a Tombstone. It wasn’t all bad, though, considering that this entire list would have been impossible without it. Snuka was still a huge name at the time, and Undertaker legitimized himself as a future superstar by defeating him.
9 BEST: WrestleMania XXVIII – Triple H
As the only man to wrestle Undertaker at WrestleMania three times, not to mention that the second two were in a row, Triple H had to do something special for the third one lest fans start getting tired of him (not that this has ever been a problem for him before). At the time, there had only been one Hell in a Cell match at the Grandest Stage of Them All, and spoiler alert, it was a huge bomb. Luckily, Triple H came to the match far more prepared than the Big Bossman, and special guest referee Shawn Michaels actually added a whole lot to the match with his continued antics. While we have to argue WWE was going a little bit too far in calling it “the end of an era” for no particular reason, the match was appropriately big and epic enough to live up to the star power involved, and violent enough to take place in 20 feet of steel.
8 WORST: WrestleMania XV – The Big Bossman
Speaking of Hell In A Cell matches at WrestleMania being a huge bomb…regardless of what sort of structure it took place in, The Undertaker’s match against the Big Bossman was bound to fail pretty much from the start. That said, shoving them inside the Cell only exacerbated the inherent problems with the pairing, most important being that Bossman was really just an avatar for Vince McMahon, who Undertaker was actually feuding. Aside from being Vince’s bodyguard, Bossman had little issues with Undertaker himself, plus he was well past his prime by the point he was slotted into the match. There was also the fact the Cell barely came into play until the ending, when Undertaker and the Brood hanged Bossman from the roof. Paradoxically, although the whole point of HIAC is for the match to redefine brutality and violence, many fans felt this was going to far.
7 BEST: WrestleMania 23 – Batista
Believe it or not, expectations weren’t particularly high heading in to WrestleMania 23, at least insofar as The Undertaker challenging Batista for the World Heavyweight Championship was concerned. On the plus side, unlike last time he got a title shot at Mania, Undertaker actually earned this one by winning the Royal Rumble, the only time he’s done so in his career. This gave them a long time to slowly build towards their match, and it was even better that Batista being champion for some time, making him look stronger than ever going into the match. Despite it all, critics were still worried the two hulking, occasionally slow moving athletes would get shown up, especially on a card that also contained Cena-Michaels. Somehow, the two not only proved all the haters wrong but also nearly stole the show, and in many respects solidified that the Streak was as or more important than any title.
6 WORST: WrestleMania XIX – The Big Show and A-Train
Right away there are some huge issues with the sole handicap match in The Undertaker’s WrestleMania Streak, least of all that it wasn’t really a handicap match. What occasionally gets glossed over in retrospect is that Undertaker technically had a tag team partner for the bout in Australian grappler Nathan Jones. It seems impossible in retrospect, but Jones was actually considered somewhat of a hot prospect at the time, hence getting to team with the Dead Man. Unfortunately for WWE and anyone who actually wanted to see the match, the company got cold feet on the night of the show and had him removed from the bulk of the contest, leaving Undertaker alone to implausibly defeat two so-called immovable objects with relative ease. Had the circumstances been different, it’s possible the match might have worked out, but given how slapdash it was, the wrestlers never really had a chance.
5 BEST: WrestleMania XXIV – Edge
One year removed from earning a World Heavyweight Championship match at WrestleMania by winning the Royal Rumble, the Undertaker looked to repeat his accomplishment by similarly winning an Elimination Chamber match. This time around, Edge was the champion going into the Showcase of Immortals, and as predicted he was now equally concerned with ending the WrestleMania streak as he was with retaining his gold. Edge certainly gave it his all during his attempt at conquering the unbeatable, and yet he too fell to Hell’s Gate after an incredible 24 minute war. Truth be told, Edge was the real star of the match, constantly countering Undertaker’s greatest and most memorable moves and his character’s reputation as the Ultimate Opportunist. Of course, that Edge was still unable to defeat the Dead Man with all his intelligence likewise left Undertaker looking even stronger, preparing him for the greatest battles of his career.
4 WORST: WrestleMania XI – King Kong Bundy
Much like when the Streak began against Jimmy “Superfly” Snuka, there really wasn’t much to it when King Kong Bundy became its fourth victim. Bundy was also a reasonably respected name, albeit less so than Snuka, leaving Undertaker with little to gain through the match. Worse than any of that was Bundy serving as an avatar for Ted DiBiase and the Million Dollar Corporation, winding up more like the Big Bossman in barely having anything to do with his own match. The real focus was DiBiase’s goons trying to steal the urn, most notably Kama Mustafa, who succeeded in doing so and thus continued the feud throughout the summer. It also invalidated whatever happened in the match, since Undertaker served nothing to gain from beating Bundy. On top of all that, Undertaker couldn’t exactly lift Bundy for a Tombstone, so the match ended with a simple clothesline, easily the least exciting of Undertaker’s victories. Well, the clean victories, anyway…
3 BEST: WrestleMania XXVI – Shawn Michaels
All great things must come to an end, and we aren’t talking about the Streak. Shawn Michaels may have ended his career at WrestleMania XXVI, but no one could say he didn’t go out with a bang, and he did it with the help of a Phenom. It started the year prior when Michaels couldn’t beat Undertaker at WrestleMania XXV, thus calling into question HBK’s self-professed reputation as Mr. WrestleMania. After the sting of defeat ate away at him nearly an entire year, Michaels made it his mission to get a second shot at Undertaker, finally getting his wish by putting his career on the line. Every minute of the match was overflowing with powerful emotion, up to and including Michaels viciously slapping Undertaker in the face and accepting his fate. One Tombstone later, and it was over, both for Michaels and one of the greatest stories he ever told.
2 WORST: WrestleMania IX – Giant González
Where does one even begin with WrestleMania IX? The event is considered almost unquestionably the worst WrestleMania in history (although maybe not the most boring), and The Undertaker’s match against Giant González strongly contributed to that reputation. In fairness to the Dead Man, it would be fair to place almost all of the blame on González, who quite frankly should have never become a wrestler. Reports indicate he didn’t much love his job, and he certainly wasn’t any good at it, too large to move around like a normal person, let alone take bumps or, you know, wrestle. The only thing González had going for him was the spectacle of his size, and sure, it looked kind of cool to see him tower over the Undertaker. It also meant next to nothing happened for a full seven minutes, until the Streak suffered its greatest indignity by continuing via disqualification.
1 BEST: WrestleMania XXV – Shawn Michaels
Depending on how you look at things, it almost came out of nowhere. Shawn Michaels and The Undertaker had been main event superstars for decades when HBK challenged the Dead Man to their first WrestleMania encounter, solely based on his desire to end the Streak. There wasn’t really anything that set this apart from any of Undertaker’s previous feuds heading into the Grandest Stage of Them All, and yet anyone with reservations about the two being able to deliver was about to receive a master class in sports entertainment. The match kept building and building until the crowd was ready to explode, and that was before Undertaker nearly killed himself less than halfway into things. That he recovered from a botched suicide dive and continued delivering the greatest performance of his life further solidified his status as the true greatest wrestler in WrestleMania history. And hey, that Shawn Michaels kid wasn’t too bad, either.