Power Ranking The Undertaker's Wrestlemania Matches

Over the course of his nearly 25 year career with the WWE, the Undertaker has become a staple for not only the promotion, but of wrestling as a whole. With only a few small tweaks to his character outside of his American Badass gimmick from 2000-2003, the Undertaker has one of the longest remaining characters in pro wrestling history.

To add further to that legendary career is the famous Streak at WrestleMania. In an athletic outlet with very few stats for fans to look at as compared to football or baseball, something like the streak gave fans something to track. It stands up there with the longest World Title reign or longest undefeated streak as a record that will be talked about for years to come. It is a legacy that literally took decades to build and because of that it has touched generations of wrestling fans, though to be honest not much of a deal was made about it until the Undertaker faced off against Randy Orton at WrestleMania 21, when Orton pointed out the fact that the Undertaker never lost at WrestleMania and he wanted to be to the first to do it, though Kane had talked about it the year prior.

So with that in mind I decided to rank the 22 matches that the Undertaker has had at WrestleMania. The ranking was compiled using a few different criteria including quality of the opponent, quality of the match itself, and the overall impact of the match, among other things. So while there are a few guys who have faced the Undertaker more than once at WrestleMania, that doesn't mean their matches will be lumped together on the ranking.

So please read, enjoy, and let us know what you think down in the comments section. Ho would you have ranked these differently? What are your favorite memories?

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22 Vs. Giant Gonzalez at WrestleMania IX

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By far the worst match the Undertaker ever had at WrestleMania was against the worst wrestler he ever faced at WrestleMania. Giant Gonzalez was the epitome of “big guy who cannot wrestle his way out of a paper bag” stereotype and this match showed how little he could do inside the ring. What is worse is that this match is the only match that Undertaker won at Wrestlemania by disqualification after Gonzalez used a rag doused in chloroform to render the Undertaker unconscious. Unfortunately no one who saw this will ever be able to expunge the image of Gonzalez in his caveman bodysuit chloroforming the Undertaker. Every wrestling fan would like to forget this one.

21 Vs. Big Boss Man at WrestleMania XV

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Another match that most would feel the Undertaker would win with ease, his match against the Big Boss Man at Wrestlemania XV. While the match had a decent buildup of the Boss Man defending his boss Mr. McMahon against the Ministry of Darkness, the idea that he could stand a chance against the Undertaker inside Hell in a Cell was preposterous. In fact, the only memorable thing from this match was when the Brood came down and helped the Undertaker hang the Big Boss Man from the ceiling of the Cell as it rose up. It's widely regarded as the worst Hell in a Cell match in history.

20 Vs. Sycho Sid at WrestleMania 13

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This match was notable for giving the Undertaker his second run as WWE champion and also for him having to be helped by another wrestler in order to win. In a couple spots, the newly turned heel Bret Hart came out to the ring to get into it with the Undertaker, Sid, and Shawn Michaels who was sitting ringside. He was targeting Sid specifically because he felt that Sid had cost him the title and would eventually hit Sid with a chair, giving the Undertaker assistance in the match. He would interfere once more against Sid, allowing the Undertaker to hit the Tombstone Piledriver to win the match. Overall it was a really weak way for the Undertaker to win, especially when it was made to seem that Sid would actually win at a couple points during the match. The saving grace was Undertaker finally becoming the WWE champion, in what was perhaps the most overdue title reign in history.

19 Vs. Big Show and A-Train at WrestleMania XIX

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Originally meant to be the Undertaker’s only tag match at Wrestlemania became his only handicap match at the event after his intended partner Nathan Jones was storyline injured earlier in the evening. The match itself was pretty uneventful and the Undertaker seemed to be doing most of the work to sell the match to the audience. The fact that the supposedly injured Jones returned to help near the end of the match did not help matters as it made the Undertaker look a little weak after holding his own against the duo of big men.

18 Vs. King Kong Bundy at WrestleMania XI

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This match was more centered around the Undertaker’s urn than anything going on in the ring. It also did not help that King Kong Bundy was a slow, power move wrestler, which left the Undertaker to carry the match. Hell, the match didn't even end with the Undertaker hitting one of his signature moves, rather only hitting a powerslam and a clothesline on Bundy to score the pin. The one positive thing it did was it set up the mystique of the Undertaker character as once he retrieved his urn he was able to get quickly recover from the Avalanche Splash of Bundy, as if he had not been harmed at all.

17 Vs. Mark Henry at WrestleMania 22

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The setup of this casket match was pretty straightforward. Henry had interfered in a title match and cost the Undertaker the World Heavyweight Title, and later claimed that he wanted to end the Streak and make a name for himself. The match was fairly lackluster, with the Phenom controlling most of the action. What makes this match so low on the rankings is the ending is that it was just so uneventful. The average fan would forget that this match even took place.

16 Vs. Jimmy Snuka at WrestleMania VII

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His first match at WrestleMania was the start of a 20 plus year streak. Unfortunately, the match suffered the effect of being on an overbooked card which featured 15 matches, so it ended in under five minutes. Also it was sandwiched in between two more important matches on the card (the blindfold match between Jake Roberts and Rick Martel and the retirement match between the Ultimate Warrior and Randy Savage) so it was seen as a time filler more than anything else, thus making it not as memorable as other matches Undertaker had at Wrestlemania.

15 Vs. Diesel at WrestleMania XII

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This match was a fairly straightforward affair between two big wrestlers, started after Diesel had cost the Undertaker the WWE Title by interfering in his match against Bret Hart, letting him win by DQ but costing him the title, as well as the rematch. Undertaker would get revenge by costing Diesel the title by dragging him into a hole in the ring while he was in a match with Bret Hart. The two would meet at WrestleMania XII where the Undertaker would beat Diesel in one of his last WWE PPV appearances before heading to WCW.

14 Vs. Triple H at WrestleMania X-Seven

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The first match of three between Triple H and the Undertaker had a good buildup and the match itself was pretty well paced, adding to the quality of the entire WrestleMania card. After Triple H had declared his desire to be in the main event of WrestleMania because he had beat everyone in the promotion, including Steve Austin and the Rock who were in the main event, the Undertaker took exception and claimed that Triple H had never beaten him, and in fact the two had never faced each other one-on-one at a WWE PPV. The two would go back and forth leading up to the PPV, finally leading to a back and forth match which included use of steel chairs and sledgehammers.

13 Vs. Kane at WrestleMania XX

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The second match between Kane and Undertaker is ranked lower than the first as the leadup to it was kind of hokey as Kane would claim that the Undertaker was dead after burying him alive at Survivor Series, (because Undertaker couldn't possibly come back from the dead, right?). The following months would see Kane seeing paranormal events such as the Undertaker’s music chiming at odd intervals, rain on the entrance ramp, and standing in the ring as it was lifted above the ground. The match itself consisted of Kane continuing to say that the Undertaker was not real before losing in under eight minutes. The real story of the match was the Undertaker's return as the Deadman, in wrestling's most famous arena.

12 Vs. Batista at WrestleMania 23

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After winning the Royal Rumble, the Undertaker decided to take on Batista for the World Heavyweight Championship. The angle would be further built upon by Batista claiming to have lost respect for the Undertaker as a competitor, eventually betraying him in a tag match against John Cena and Shawn Michaels. The match was a back-and-forth affair with the Undertaker eventually scoring his 15th straight WrestleMania victory after he hit Batista with the Tombstone Piledriver, at the same time becoming the first wrestler to win both the WWE Championship and World Heavyweigtht Championship at WrestleMania.

11 Vs. Jake “the Snake” Roberts at WrestleMania VIII

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A match made solely on the psychology and story behind it, the Undertaker’s second ever match at Wrestlemania comes in at 11. The story between the Undertaker and Jake “The Snake” Roberts started after Taker prevented Roberts from hitting Miss Elizabeth with a steel chair. Roberts would demand answers in an interview segment with the Undertaker, but would hit his DDT finisher on Paul Bearer and slammed the Undertaker’s hand in a coffin door and hit it with a chair after he did not like the Undertaker’s response. The match itself was under seven minutes, but the match and its buildup allowed the Undertaker to establish himself as a face in the WWE.

10 Vs. Brock Lesnar at WrestleMania XXX

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Now if this match had ended another way, it would have been ranked a bit lower than what it currently is. Yet, this is the match where the Streak was ended and for that alone it earns its spot at 10. While the buildup to the match was done well, with Lesnar complaining about not being in the WrestleMania main event, but being given a match against anyone else of his choosing at the event, leading to the return of the Undertaker who would sign the contract with Lesnar before stabbing his hand with the pen they used to do it.

The problem with the match is that no one really expected a part-timer like Lesnar to win the match and the match followed the formula of other recent Undertaker streak matches where the competitors traded finishers before the Undertaker eventually picked up the win. Yet when Lesnar finally got that pin and the Streak became 21-1, you could hear a pin drop in that stadium, as the shock washed over the audience. It was definitely a moment that will live in the memories of wrestling fans and because of that it earns its spot in the rankings.

9 Vs. Edge at WrestleMania XXIV

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After Edge cashed in the Money in the Bank contract on the Undertaker to win his first World Heavyweight Championship, it was a forgone conclusion that the two would meet in a one-on-one match later down the road for the belt. The Undertaker would earn that shot after winning a number one contender’s match at the previous PPV and the two would face off in the main event of WrestleMania. The match itself started off slow but picked up as members of Edge's entourage interfered and Edge used every dirty trick he could to try and beat the Undertaker. The end would eventually come though as the Undertaker would lock Edge in the Hell’s Gate as Edge attempted to spear the Undertaker, causing Edge to tap out.

8 Vs. Kane at WrestleMania XIV

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After it was revealed that the Undertaker’s storyline brother Kane was still alive and wanting revenge against the Undertaker, a match between the two was set for WrestleMania XIV. With both men portraying unstoppable demonic beings, it was an interesting idea to see who would come out on top. Both men traded power moves before the Undertaker hit a series of moves including three Tombstone Piledrivers before Kane would stop rising long enough to be pinned. Kane would then attack Taker with a chair and hit a Tombstone of his own on top of the chair, but the Undertaker would rise up himself. The match worked well as it established Kane as a serious threat to anyone in the ring as well as solidified the mystique of both wrestlers as unstoppable monsters.

7 Vs. Ric Flair at WrestleMania X-8

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This match between two living legends was a WrestleMania dream match for fans and it had a pretty good buildup to the actual match. After Ric Flair declared disgust in the Undertaker’s recent actions against the Rock, the co-owner of the WWE would interfere in the rematch between the two men, costing the Undertaker the match. Taker would challenge Flair to a match, which he refused stating that he was no longer a wrestler, leading to the Undertaker tormenting Flair’s family and friends which eventually led to Flair accepting the challenge. The No Disqualification match saw the use of weapons and interference from Flair’s friend Arn Anderson, but ultimately the Undertaker got the win and went 10-0 at WrestleMania.

6 Vs. Randy Orton at WrestleMania 21

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The year when “The Legend Killer” Randy Orton went after the Undertaker at WrestleMania was when the aura of the Streak really came to the forefront for wrestling fans. Claiming he would be the one to end the Streak, Orton would torment the Undertaker and the WWE in general leading up to their WrestleMania match. The match would see Orton’s father, “Cowboy” Bob Orton interfering on his son’s behalf and Orton even attempting to hit the Tombstone Piledriver on the Undertaker. This would be reversed though and the Undertaker would hit the Tombstone himself to become 13-0 at WrestleMania.

5 Vs. Triple H at WrestleMania XXVII

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In maybe the most simplistic setup for a match in wrestling history, the Undertaker and Triple H agreed to their second WrestleMania match without saying a word to each other. All they did was look up at the WrestleMania sign and nodded to each other. It was further built upon as Triple H was looking for revenge against the Undertaker for him being responsible for forcing Shawn Michaels into retirement at the previous year’s WrestleMania, as well as being able to succeed where his friend had failed twice prior. The match featured back-and-forth action along with strong psychology and emotion from both men. The end result of Triple H tapping out to the Hell’s Gate, leaving both men physically shaken to the point where the Undertaker needed assistance to the back just capped off the match of the night.

4 Vs. CM Punk at WrestleMania XXIX

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Known more for the technicality of the match and the sudden backstory, the match between the Undertaker and CM Punk comes in at number four in the rankings. After the Undertaker gave an open challenge to anyone who dared to face him at WrestleMania, CM Punk won the chance after beating Sheamus, Randy Orton, and the Big Show in a fatal four-way match on Raw. Then in an unfortunate coincidence, the Undertaker’s former manager Paul Bearer died due to respiratory issues. This was then used as a starting point to build the feud between Punk and Taker, going so far as to have Paul Heyman come out dressed as Bearer and stealing the Undertaker’s urn in order to get into the head of the Undertaker. The match had both men hitting the other with everything that they had, sharing close finishes and attempts at their respective finishers. The Undertaker would finally get the win after hitting the Tombstone Piledriver on Punk after they traded attempts at their finishers.

3 Vs. Triple H at WrestleMania XXVIII

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After their No Holds Barred match at WrestleMania XXVII, Triple H felt that there was still unfinished business with the Undertaker, especially after seeing that the Undertaker needed to be assisted from the ring after their match. It was finally agreed upon that the Undertaker would face off against Triple H in Hell in a Cell with Shawn Michaels as the guest referee.

The match itself was an all out war which featured finishers from all three men, including a Sweet Chin Music into a Pedigree combination that had fans holding their breath thinking that it would be the move to end the Undertaker’s streak. The match itself was really good, but it was the emotion and psychology of it that took it over the edge, with the image at the end of Michaels and the Undertaker helping Triple H up the ramp in a show of respect after the match as the cherry on top.

2 Vs. Shawn Michaels at Wrestlemania XXV

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After beating JBL at No Way Out and then Vladimir Koslov on RAW for the chance to challenge the Undertaker at WrestleMania, Shawn Michaels began to play mind games with the Undertaker. Playing off a light versus dark angle, Michaels came to the ring covered in a glowing light and wearing attire similar to the Undertaker’s, though all white. The match was a technical feat as both men took it to each other for 30 minutes, finally ending as the Undertaker caught Michaels as he went for a moonsault and hit him with the Tombstone Piledriver. The match would be named Match of the Year by Pro Wrestling Illustrated and Wrestling Observer Newsletter.

1 Vs. Shawn Michaels at Wrestlemania XXVI

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A year after their legendary match at WrestleMania XXV, Shawn Michaels wanted another crack at the Undertaker. The Undertaker felt he had nothing left to prove to Michaels and declined, but would fight him if Michaels won the Royal Rumble and was given the option to challenge the Undertaker for his World Heavyweight Championship. It seemed like Michaels had victory in his grasp at the Rumble but would eventually be eliminated by Batista. Michaels would then goad the Undertaker into the rematch by interfering in the Elimination Chamber Match for the World Heavyweight Title, costing the Undertaker the title. The Undertaker agreed to face Michaels in a rematch, on one condition. He wanted Michaels to retire if he lost again.

The two would battle for almost another 25 minutes, trading blows and finishers, but with neither willing to stay down. In the end, the Undertaker could be heard yelling at Michaels to stay down but Michaels would have none of it, finally slapping Undertaker, sending him into a rage, making him hit a third Tombstone Piledriver and pin him. Michaels would get his sendoff from the fans and the match would be called another classic between the two. The emotion this match evoked from fans gives it the no.1 spot.

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