When wrestling fans look back on all the great and amazing superstars, matches, pay-per-views and moments that have happened there’s so many that come to mind. There’s also some moments or matches that outgrow the very people that create them, just look at Hulk Hogan and Hulkamania during its peak. There is however one single entity that is so incredible that once it’s put into perspective it’s an astonishing achievement, and that entity is The Undertaker’s 21-0 undefeated streak at WrestleMania!
It’s such an amazing feat that no other wrestler from any pro wrestling company on earth will ever even get close to matching. The fact the same professional stayed with the same company for well over 20 years is unbelievable on its own but when you imagine that he’s also been allowed to build-up this winning streak for all this time it’s just phenomenal in my opinion. Ever since WrestleMania VII, The Undertaker comes back year after year and if anything he gets better with age even though physically his body is hurting. In 23 years “The Phenom” has only missed two WrestleMania Pay-Per-Views (X and 2000).
It is however fair to say that not all of “The Deadman’s” WrestleMania matches have been first-class but the great matches he’s had at the “Granddaddy of em all” more than make up for the few bad ones. Here in this article myself and regular thewrestlingmania.com writer Matthew Roberts have put together this list ranking The Undertaker’s 21 matches at the biggest show of all and after much thought, and some help from the great fans on the Facebook group page WWE Prediction Leagues, here’s the verdict….
21 – vs. Giant Gonzales: WrestleMania IX
It should come as little surprise that the Worst WrestleMania Of All Time™ should provide the worst match of the Undertaker’s famed Streak. There’s an argument that Jorge “Giant” González is the worst ever professional wrestler and whilst that might seem a bit harsh, the failed basketball player was truly awful, offering up nothing but a tall lanky frame. The WWE even had to paint muscles on his bodysuit. The match itself was diabolically bad and remains the only Streak match to date where The Undertaker didn’t win clean, instead winning by DQ when Harvey Wippleman passed a “chloroform soaked” rag to Gonzales which he used to knock out ‘Taker. Naturally The Undertaker recovered. A terrible match, made all the more terrible by the non-decision finish and the fact that a WrestleMania match was used as a set-up bout to prolong this dire feud until SummerSlam.
20 – vs. King Kong Bundy: WrestleMania XI
This came about when the Million Dollar Corporation stole The Urn from our man. It offered very little other than the then-traditional style of Undertaker fighting a pretty useless big man, struggling for a bit and then coming back and winning. This is so unmemorable that I even forgot that American League baseball Umpire Larry Young was the special guest referee. It was a storyline based around the Major League Baseball strike at that time, although the strike had ended prior to ‘Mania. The Undertaker got the Urn back from Ted DiBiase during the match, only for Kama to steal it back again. So this is the second consecutive ‘Mania match that was pretty much used to set up a SummerSlam match.
19 – vs. Big Boss Man: WrestleMania XV
How can you not love a Hell In A Cell match that ends with the hanging of one wrestler? You wouldn’t get that in the PG era. Surprisingly the Boss Man survived to continue his wrestling career. The match was pretty poor as the Boss Man was well past his peak here and it remains one of the weakest Cell matches there has been. As a stand-alone match it is pretty unmemorable. It does have a certain kitsch value though as part of the on-going Ministry/Brood/Higher Power storyline that would dominate WWE storylines during this period.
18 – vs. “Superfly” Jimmy Snuka: WrestleMania VII
People complaining about current WrestleMania’s obviously don’t remember the days when even the biggest show of the year was filled with virtual squash matches. (This match was less than five minutes long…and there were still four other matches on the fourteen match card that were shorter!) There was no real storyline build up to this one, it was simply a matter of the new guy taking on the grizzled company veteran. Of course as pedestrian as the match was, it’s historic value as the opening match of The Streak is vibrant and strong. I also have a fondness for this match as it was part of the first WrestleMania I watched in full when I was a kid. And at the time, this eerie (relative) newcomer systematically destroying the legend was pretty damn cool.
17 – vs. The Big Show & A-Train: WrestleMania XIX
I have to admit bias here. I was at this event at Safeco Field, Seattle and so I personally would have had this higher in the list, but we here at TheWrestlingMania are nothing if not democratic (Matthew). It wasn’t the greatest technical match of all time and perhaps does suffer from being on a card that had a good sprinkling of much better matches, but the effort from The Undertaker here was something to behold, as if he realised that he had to come up with something pretty special to avoid the bout sinking without trace. It was a wise decision to nix the awful Nathan Jones from the bout (he was scheduled to be Taker’s tag team partner) and the two-on-one nature of the bout added to the drama. This was from the days when it was still relatively conceivable that The Streak could come to an end. Given the expectations going into the match, this was one hell of an effort from The Undertaker.
16 – vs. Mark Henry: WrestleMania 22
When he debuted in 1996 I don’t think anyone could have envisioned that Mark Henry would have such a long career in the WWE and that he would climb his way to winning a World Title. You probably could have predicted that he would one day be a victim of The Undertaker at WrestleMania based simply on his size. Of course by WrestleMania 22, the “old” formula for the Undertaker had been long been somewhat superseded as our man was allowed to break out more wrestling and have matches that didn’t simply revolve around him being beaten up and making the big comeback. Compared to the previous couple of years, this was something of a throwback but as an old school style Casket Match it had its certain charm and was once again noticeable for The Undertaker putting in a supreme effort against less than capable opponents. And hey, once his next feud was revealed to be against The Great Khali, this seemed like a five-star classic.
15 – vs. Sycho Sid: WrestleMania 13
It’s not harsh in the slightest to admit that this was a WrestleMania title change that got totally lost in the annals of time. WrestleMania 13, of course, is about one match and one match only in the form of the genuine five-star Bret Hart/Steve Austin classic. As with anything involving Sid, this isn’t a great technical masterpiece but neither did it try to be. Shawn Michaels added very little on commentary and the interference of Bret Hart only clouded issues as well (but was acceptable within the “no disqualification” rules of the match). That said, it has historical importance as it was the start of Undertaker’s second World Title reign (and arguably his first “proper” one) and his first as a babyface. And it did provide the desired reaction from the fans on the night.
14 – vs. Jake “The Snake” Roberts: WrestleMania VIII
Again, you would be hard pressed to say that this was a technical tour de force. But it has a certain something about it and provides something that is often missing from the WWE today. Revenge. The Undertaker became the good guy after rescuing Randy Savage and Miss Elizabeth from a planned attack by the Snake, but Roberts paid him back by trapping his hand in a casket, smashing Paul Bearer with a DDT and then waffling the Dead-Man with a few steel chair shots to boot during a Funeral Parlour. Here, The Undertaker would exact the perfect revenge. Jake took it to him in the early going, but our man survived two DDT’s to hit back with a Tombstone Piledriver on the arena floor to gain the win by pinfall when he rolled the unconscious Roberts back into the ring. OK, the “hard concrete” of the arena floor was actually what looked like about 10 inches of sponge padding, but it was still something to behold at the time. As a way for The Undertaker to vanquish the oily and slimy Snake, this was just what the doctor ordered.
13 – vs. Diesel: WrestleMania XII
At a time, just before the feud with Mick “Mankind” Foley, when The Undertaker wasn’t exactly known for his great matches as a whole, this was actually a very good effort, all things considered. The build up, where both men had cost the other World Title matches against Bret Hart was quite good and heightened the tension between the two men. At over fifteen minutes long, this was by far the longest match that The Undertaker had had at WrestleMania to date and was a very good “big man” battle. The opening back and forth exchanges were really exciting and if it did slow down towards the end, it was still a heated battle that thrilled the fans. Undertaker survived two jack-knife’s from Big Daddy Cool and was ultimately victorious with the Tombstone Piledriver. Whilst not up there with what The Undertaker would deliver in the years to come, this was a very good match and is up there with the greatest “straight” singles matches Diesel would ever have.
12 – vs. Kane: WrestleMania XX
There are better matches, from the in-ring perspective, to be found ranked lower but for pure spectacle, this encounter deserves moving up to its position on this list. The Undertaker had been absent since the preceding Survivor Series 2003 show (where he had been, lest we forget, buried alive) and there was genuine anticipation as to exactly what the Undertaker would return as. It proved to be a return to the “dead-man” gimmick of old, complete with the reappearance of Paul Bearer. The match itself was little more than an extended squash match and yet as a vehicle to reintroduce the “old” Undertaker it more than did it’s job.
11 – vs. “Nature Boy” Ric Flair: WrestleMania X8
This was a very decent match between two of the biggest names in pro wrestling history. The build-up was fantastic with Taker pushing Flair into the match by attacking Flairs son. Even though I was a big Taker fan there was a small part of me that wanted the Nature Boy to win the longer the match went, but it was not meant to be. After Taker won the match he held up his hands to show us the first real acknowledgement of The Streak when he held all 10 of his fingers up, something big was getting recognised.
10 – vs. Batista: WrestleMania 23
This World Heavyweight Championship match came about after the Phenom finally won the Royal Rumble match and then chose Batista to face at WrestleMania. On paper the match really shouldn’t have been very good because to big men going one on one isn’t usually a great match but this match was different, it had that little bit extra that made it a great match in my view. We all know the Undertaker won the match and title but Batista pushed him all the way and for a short time during the match I was once again thinking to myself that Taker was going to lose, but once again he proved me wrong.
9 – vs. Randy Orton: WrestleMania 21
I remember the build-up to this match and thinking Randy Orton is definitely going to win. Remember, The Streak wasn’t the big deal back then it is now. Back then Orton was on his Legend Killer form and he was more than making a name for himself which took us nicely into this feud. The match itself was a lot better than its sometimes given credit for and in my opinion even though Orton lost it was the night the young man really came of age. Right up until Taker hit that final Tombstone I though Orton got this but I’m now pleased I was wrong because we wouldn’t now have the legendary winning streak that the Undertaker possesses.
8 – vs. Triple H: WrestleMania X-Seven
This was the first in the trilogy of brilliant matches between the two men and was in my opinion the best match they had from the 3 in terms of the actual wrestling quality. It was The Undertaker’s first match in his immortal WrestleMania winning streak in his American Bad Ass gimmick. The build-up was very good with Taker trying for the match and once we got to the night of WrestleMania X-Seven itself it was just another top draw match, like many others on that iconic night of wrestling. The match was brutal with both men laying it all on the line. The action left the ring and went way up into the crowd at one point with the fans really getting into the match. Once back into the ring not even the trusted sledgehammer of HHH could stop the Undertaker gaining his victory via way of a Last Ride. It was a great match and one that was right at place on what was arguably the best WrestleMania of all-time.
7 – vs. CM Punk: WrestleMania 29
What a match! What an outstanding match! Just a couple of weeks ago at WrestleMania 29 in front of over 80,000 people the near 50 year-old Undertaker proved that even though his body is hurting he can still come out and steal the biggest show of them all. Along with the great talent of CM Punk, Taker put in a display that some other superstars past or present could only dream of. The build-up was short but controversial, with the sudden passing of Paul Bearer being brought into the feud. The match itself more than stole the show and once all was said and done it was the streak extending to 21-0 with the help of a big Tombstone.
6 – vs. Triple H: WrestleMania XXVII
If ever there was a time when I thought the Streak was over it was during this match without a doubt! This match was just immense and HHH hit Taker with everything he had from Pedigree, after Pedigree, to numerous chair shots and even executing Tombstone of his own. The near falls were unbelievable and kept the crowd on the edge throughout the whole match. In the end we saw the Undertaker go 19-0 at WrestleMania and defeat HHH for a second time at the event by applying Hells’ Gate and making HHH tap out , but in a shocking twist it was the Undertaker that had to be helped from the ringside area. A year later Taker would try and claim revenge for what happened after this match, but that’s still to come…
5 – vs. Edge: WrestleMania XXIV
Going into this closing match of WrestleMania XXIV the Undertaker was 15-0 and looking to not only take that record to 16-0 but also to regain the World Heavyweight Championship. To reach WrestleMania and his shot at the title the Undertaker won an Elimination Chamber match at the WWE Pay-Per-View No Way Out by last eliminating Batista. The two men then embarked in a bitter but entertaining feud leading up to the match. The match was a class and definitely one of the best both men did on the biggest stage. After many failed attempts at putting the other away it was the Undertaker that won with his Hells’ Gate submission hold, thus once again becoming champion and also taking his Streak to 16-0.
4 – vs. Kane: WrestleMania XIV
If ever there was a feud to be settled at WrestleMania this was it. It all started with Takers former manager Paul Bearer claiming that the Undertaker was a murderer who killed both his parents, plus his younger brother Kane by setting the family home on fire. The big shock for Taker was the claim from Bearer that Kane was still alive. Then during the first ever Hell In A Cell match between Shawn Michaels & Undertaker, Kane came out and delivered a Tombstone to his older brother resulting in Taker losing the match. In the coming months Kane would try to force his brother into a match but Taker refused to fight his own flesh and blood. Refuse that is until Kane would once again cost the Undertaker a match against HBK this time during a Casket match. After the match Kane would set fire to a locked casket that Taker was believed to be in. This lead to Taker accepting the challenge and the two men would face each other at WrestleMania XIV. The match was a gritty and hard hitting match that the Undertaker would win with a combination of Tombstone finishers. It was a feud worthy of a mention near the top of any list of feuds in WWE history and is certainly an unforgettable one.
3 – vs. Triple H: WrestleMania XXVIII
There’s moments in wrestling history where you look back and say “That was awesome”, and this match is definitely one of them. The build-up was great, the match was great, and the show of respect after the match was simply wrestling at its very, very best. In a match billed the end of an era it also included Shawn Michaels as the special referee. Before the match even started we got a first look at Taker without his legendary hair and the crowd showed their appreciation from then on in. The match that followed was awesome especially when you take into account that both men were well into their 40’s and that Taker was still recovering from a year off from having surgery. I think its what happened after the match that stole the entire show when all 3 men helped each other to the back and then turned to acknowledge the crowd, just first class in my opinion. Great match and a great memory.
2 – vs. Shawn Michaels: WrestleMania XXVI
Some wrestlers retire from injury, some from age, and some because of personal problems. At WrestleMania XXVI however HBK retired in just the way he wanted and against the superstar he wanted. In many fans eyes Ric Flair got the ultimate send off and I agree with that to a point, but if it’s based on the quality of the match in which you retire, this match wins hands down for me. A year after trying to end the Undertaker’s legendary WrestleMania winning Streak and failing, Shawn became obsessed with breaking the Streak and set how for his rematch. He tried in vain to win the Royal Rumble so he could face the then World Heavyweight Champion The Undertaker at WrestleMania to claim revenge, and when that didn’t work he cost Taker the championship at the Elimination Chamber PPV. After losing the championship the Undertaker agreed to face Shawn one last time but only if it was a Streak vs. Career match, which HBK accepted. Both men put on a great match that more than just stole the show, it beat almost any match you will ever witness. The two men wanted to produce something special to send Michaels’ career off in style and they more than did that. It was so close at times you could almost feel it coming through the television watching from home, and that’s no exaggeration! In the end it was the great career of Shawn Michaels that was ended and after an emotional embrace with Taker after the match Shawn said his farewells to not just the fans in attendance that night, but fans the world over!
1 – vs. Shawn Michaels: WrestleMania 25th Anniversary
You guessed it! This is the ultimate wrestling match and it was this match that came out by far the winner with almost perfect scores. It’s the match that even non wrestling fans could watch and still massively enjoy. The appreciation from the fans in the arena that night tell you all you need to know and after the match that the two legendary icons put on its no wonder the respect poured from the crowd. All the young pretenders came to steal the big 25th Anniversary of WrestleMania but it was the two legends that proved the masters on the night. The match had so many near falls and close finishes, plus kick outs from both the Tombstone from Michaels and Sweet Chin Music from Taker. The match finished when Taker caught a moonsault from HBK and punished him with yet another Tombstone. I’ve been a wrestling fan since WrestleMania III and I can honestly and wholeheartedly say that this match between the Undertaker and Shawn Michaels is the best match I have ever seen.
– By Matthew Roberts
