The Undertaker's Best Wrestlemania Matches, Ranked By The Wrestling Classic

Wrestlemania 9 gets a lot of hate for many reasons, one of them being the Undertaker being put in a match against Giant Gonzales. There was only so much the Undertaker could do to carry the big man in a suit with airbrushed muscles and hair. For those fortunate enough not to be familiar with Giant Gonzalez, he was basically a less mobile Great Khali. I wasn’t sure Undertaker could tombstone Gonzalez, but even less sure if Gonzalez was skilled enough to take the move. They ended up going with a DQ finish after Gonzalez smothered Taker with an ether-soaked rag. Therefore, the Undertaker still technically won by disqualification. If for any reason Undertaker had lost here by count-out or something, there might have never been a streak. Thankfully that wasn't the case.

Wrestlemania 11 is another show that could be considered the worst Wrestlemania of all time. However, the year 1995 was a weird year for professional wrestling across the board. The Phenom was pitted against members of Ted Dibiase's "Million Dollar Corporation" in a never-ending rivalry that started in 1994 and concluded at the end of 1995, with the rivalries usually surrounding them stealing his magical urn that was usually in the hands of Paul Bearer. King Kong Bundy was the member of the corporation to face the Undertaker at Wrestlemania. King Kong Bundy was an under-appreciated big man in the 80s and early 90s. He even headlined Wrestlemania 2 against Hulk Hogan. However, he lost a step by this time and was a lot less mobile, which made this a painfully slow match even at six minutes long.

It was a bummer that we only got this Ministry incarnation of the Undertaker character at one Wrestlemania. I always felt like this was his most sinister and scary look. It's even more of a bummer that he appeared with this look one time at Wrestlemania for such a mediocre match. The fact that I would have to really look up the build-up for this match, because I can't remember it, tells you there really wasn't one. Undertaker was feuding with the Corporation and Big Bossman was part of that faction. This was basically just an extended brawl and arguably the worst Hell in a Cell match of all time. I also think the only reason it was in the cell was so they could pull the stunt at the end where they basically had the Undertaker and The Brood perform a fake murder by hanging the Big Bossman from the roof to the cell to leave the fans with a lasting visual that we would rather forget. This was memorable for all the wrong reasons.

Wrestlemania 7 was The Phenom's first appearance on the grandest stage of them all. He faced off against a popular legend who had already cemented their legacy in the 80s in "Superfly" Jimmy Snuka. The Undertaker was still fairly new to the scene as he just made his debut at the Survivor Series four months prior. This was basically a quick match to showcase him on the big show, which they did really well. This was the early days of the Undertaker where his character wouldn't sell anything but also barely performed any high impact moves. There was nothing wrong with this match; it achieved exactly what they intended it to achieve, but it was still just a high-profile squash match.

This was the only time the Undertaker was in a handicap situation for Wrestlemania. He was originally paired up with the big Australian Nathan Jones that the WWE had recently signed due to his great look and character, but he had absolutely no wrestling ability. There were rumours it was supposed to be Jones versus Taker before the tag match against Big Show and A-Train was the final decision due to not knowing how well Jones could perform. In the end, they aired an angle where Jones got attacked earlier in the night leaving The Undertaker to fend for himself. The entrance for Big Evil with Limp Bizkit performing his "Rollin'" theme song was awesome. The match was decent for what it was and Jones made an appearance near the end to even the odds, but overall this felt like an underwhelming way to feature the Deadman at Wrestlemania.

The match against Roman Reigns from Wrestlemania 33 is ranked this low for multiple reasons. It was one of those matches that took place after Taker was defeated at Wrestlemania, so he was no longer defending the streak. However, they were able to create a compelling storyline where it seemed as if the Undertaker was going to pass the keys to his "yard" to Roman Reigns. Whether you liked Roman Reigns at the time would also dictate how you felt about this match. As someone who didn't dislike Roman Reigns, the predictable outcome didn't really bother me. The problems with this match had more to do with how hard it was to watch, as The Phenom looked off his game even though Reigns tried his best to help him throughout the match. Also, this was supposed to be Undertaker's final farewell match yet nobody wanted to see him go out this way. There was an entire spectacle following the match where he left his gloves, jacket and hat in the ring as if this was it, only to return the next year to redeem himself. 

Wrestlemania 8 was Undertaker's second Wrestlemania and he was put up against a formidable opponent in Jake "The Snake" Roberts. Looking back at it, it's very possible the streak could have never happened if the more established Jake Roberts went over in this match by stealing a huge win or by DQ. However, Roberts was on his way out of the company and the Undertaker was a babyface for the first time in his career. Roberts did get in some offence unlike Snuka the year prior, which Undertaker sold a little for. This included Undertaker taking one of Roberts iconic DDTs—when the move was still a finisher—that The Undertaker sat up to, sending the Snakeman into shock. This match was good for what it was and another established legend put over Undertaker to make the Deadman look stronger.

As far as we knew, The Undertaker had officially retired after Wrestlemania 33 after a rough match with Roman Reigns. When Wrestlemania 34 came around, the rumours of Cena challenging Undertaker started swirling on the interweb. Cena spent months teasing a match with the Undertaker and calling him out with no match officially booked. They even went to the extent of having Cena show up at Wrestlemania as a "fan" with hopes that Undertaker would make his decision last minute, thus never actually booking the match prior to the show. I speculated that Undertaker would return in his American Badass character due to him leaving his Deadman gear in the ring the year before, however that wasn't the case. Two of the biggest stars in professional wrestling battled for the first time since 2003 in a two minute match which allowed The Phenom to redeem himself. He explained on The Last Ride documentary in 2020 that he hated his performance so much the year prior that he decided he couldn't call it a career on such a sour note. This was the squash match to redeem himself. The Undertaker looked great, but a match of this calibre deserved more time.

This was the Undertaker's first time in the main event of Wrestlemania. He was the challenger for the WWE Championship against fellow big man, Sycho Sid. This was a decent big man match but both men usually worked better with smaller opponents. Although there were a handful of big guys Undertaker did have great matches against, the list of monsters and giants that he had bad matches with is far longer. Sid had great matches just months prior against guys like Bret Hart and Shawn Michaels. Speaking about Hart and Michaels, they were initially supposed to main event this show, until plans changed due to Michaels dealing with a knee injury. HBK ended up on commentary for this match and a heel Hitman also made his presence felt during the match. It was Undertaker finally capturing the championship for the first time since 1991 that made this match memorable. I remember being excited for that.

As I mentioned earlier, the WWE loved putting Undertaker up against other big men, giants and monsters. I am guessing that is why they thought Mark Henry would be a great opponent for the Undertaker in 2006. I mean, he was a big dude and the World's Strongest Man. I remember being underwhelmed back in 2006 with the choice of opponent. This was before the "Hall of Pain'' era when I might have been more excited for this match because Henry had a ton of momentum then. Also, the Undertaker wrestled Randy Orton the year prior in a memorable match and it didn't seem like this one could follow up. They even added the casket match stipulation that meant the Undertaker could have technically lost without being pinned or tapping out. Watching the match back, it wasn't as bad as my younger self made myself believe but still didn't feel Wrestlemania worthy. Henry said they discussed ending the streak here, but thankfully the Undertaker picked up the win.

The streak had ended the year prior and the Undertaker left Wrestlemania 30 in bad shape. Nobody was sure if we would see him anytime soon, especially the following year, due to the streak being over. Leading up to the event, Bray Wyatt began calling out The Undertaker to defeat him so he could truly become the new face of fear. The rest was history. The match was just alright, but it was more intriguing to see the two supernatural characters clash. Undertaker didn't appear for the entire build up either as it was carried by Bray's promos so people were anticipating seeing The Phenom a year after the streak was broken. Bray's character had been a bit damaged up to this point from previous storylines, so I was low-key rooting for him since the streak was already over. Although looking back now, it was more important to show that the Lord of Darkness wasn't done yet just because he had been defeated at Mania. Bray would disappear after this for a bit until later in the year, while the Undertaker reappeared months later to feud Lesnar.

This was that match. The one that will go down in infamy as it was the night the Undertaker's undefeated streak came to an end at the hands of Brock Lesnar—a superstar Undertaker helped put over years back and never beat before. The Undertaker got knocked out early on in this match; we later found out he suffered a severe concussion. Lesnar did his best to walk a visibly woozy Undertaker through the rest of the match that they intended to make worthy to end the streak but suffered because of the concussion. At this point of the streak, I think us fans truly believed that the Undertaker was going to retire with the streak intact so this was a shocking moment indeed. The moment Lesnar picked up the win, the crowd was stunned and there was a deafening silence in a sea full of shocked faces. People thought it was a mistake or an audible. Nobody could believe that the streak was actually over. It was also a shame in my eyes that he lost it to someone as established as Brock Lesnar. Many thought this was going to be the Undertaker's final match, but that wasn't so.

This was the night the Undertaker returned to the dark side on the 20th anniversary of Wrestlemania. When Undertaker returned to the WWE in the year 2000, he debuted his new, more humanized biker character as the "American Badass" leaving the mythical powers of the "Deadman" behind. At Survivor Series 2003, Kane aided Vince McMahon in burying alive the Undertaker, which ended that version of the character. After months of teasing us, the Undertaker returned at Wrestlemania in Madison Square Garden along with Paul Bearer to face off against his brother Kane. The entrance alone was surreal and something we all anticipated for months. This was not meant to be compared to the 1998 encounter between the Brothers of Destruction. This match was more about the Undertaker returning to the dark side rather than trying to achieve a five star classic. The Undertaker played all his greatest hits and picked up the victory, leaving the fans satisfied with his return. It might not have been a great match but it was definitely a great Wrestlemania moment.

The match at Wrestlemania 32 usually gets a lot of hate but I think I was just excited to have Shane O' Mac back after a seven year absence. The WWE roster was filled with a plethora of injuries around the time of Wrestlemania and they needed a marquee match for The Undertaker. Shane McMahon returned, looking for full control of the company, but Vince McMahon wanted his son to beat a handpicked opponent to gain it. Vince picked The Undertaker and to make it more difficult, he made it a Hell in a Cell match. The match was slow at times for sure, but every slow period led to another dare devil stunt or hectic bump from Shane McMahon. I know it bothered people that Undertaker would have such a hard time beating someone who wasn't a full time wrestler in the first place and hadn't been around for seven years, but I was satisfied with it due to knowing this wasn't The Phenom in his prime. The Undertaker picked up the victory after Shane's insane bump of jumping off the top of the cell. I think that made it all worthwhile.

Most of the matches the Undertaker had at Wrestlemania in the early to mid 90s were all already ranked because they weren't that great. There were a couple of squash matches and a handful of matches where The Undertaker fought off giants, but they just didn't click that well. That wasn't the case with Diesel at all. Diesel usually had his better matches with smaller guys such as Bret Hart and Shawn Michaels too rather than the larger superstars, but it worked for these two. This was Diesel's final Wrestlemania before leaving for WCW a couple of months later and there were rumours that he would have beaten the Undertaker if he wasn't leaving. It was also interesting they put Diesel in such a prominent match where he got a ton of offense, rather than being involved in a one-sided squash with knowledge that he was leaving. The match exceeded expectations and they told a great story even though it felt slow at times. This was his best Wrestlemania match of the 90s and nobody expected it to be.

This was the second time The Undertaker was in the main event of Wrestlemania and it was for a World Championship again. The Undertaker was defending his streak against someone else who had never lost in singles competition at Wrestlemania in Edge. These two had a history going back to when Edge cashed in his Money in the Bank on Undertaker after last year's Wrestlemania. Edge eventually had to vacate the title due to an injury. The Rated R Superstar returned at Survivor Series to cost Undertaker the championship before winning the championship himself the next month. Undertaker didn't just want the championship but retribution as well. This match was the main event on a really stacked card, which included Ric Flair's retirement match against Shawn Michaels, but they still really delivered. The match started off slow but had great storytelling the entire time. In the end, Edge tried everything a desperate slimy heel would to defeat The Undertaker, but none of his shenanigans or plans worked. The Deadman eventually caught Edge with a Tombstone to win the World Championship as the crowd popped.

This match is ranked higher than Undertaker-Diesel only because of the anticipation we all had for it. It was the first ever encounter between the Undertaker and Kane. Undertaker-Diesel might have been a better match, but Undertaker-Kane meeting for the first time was a bigger spectacle. The storyline was one of the most interesting aspects of television every week and Kane spent months trying to get his brother to fight him, even if that meant setting his own brother on fire to get him to accept. This wasn't an all time classic, but seeing the Undertaker face off against someone who possessed some of the same powers and strengths as he did was something we had never seen before. Kane up to this point seemed indestructible so it was intriguing to see how Undertaker was going to overcome the odds. This might have been Undertaker's biggest threat to the streak up to this point. The rowdy crowd added to the atmosphere and helped the Undertaker find a way to defeat his brother in an unforgettable battle.

In a feud that started overseas, it became clear that AJ Styles would wrestle the Undertaker at Wrestlemania. Unfortunately, this was the Wrestlemania that almost didn't happen because of  the global coronavirus pandemic. However, the WWE found a way to make sure the show went on by holding the event in their very own performance center, rather than in Raymond James Stadium like planned. The two were scheduled to have a regular singles match, which is a match that would have been something special if it took place a decade earlier. Better late than never, right? Regardless, I don't know if I was that excited to see a modern day Undertaker face off against AJ Styles in the ring. 

Thankfully, the pandemic allowed them to get creative and we got an amazing cinematic Boneyard match—basically a buried alive match—between the two. This allowed them to showcase the Undertaker in such a positive light by working around his limitations caused by older age and years of injuries. The Phenom also got to bring out his "American Badass" persona too for this match and he was a mesh of all of his characters. The Undertaker stood tall at the end of this fun piece of art, and once again we believe he rode out into the darkness one last time as he has stated that he is actually retired now.

This was my least favourite of the Undertaker-Triple H Wrestlemania trilogy. I don't know if it fell victim to being on a poor show or if people only liked it a lot because it was the best match on an overall mediocre show. Regardless, Triple H was a seasoned veteran now and Undertaker seemed to be slowing down. After two straight years of classic matches against Shawn Michaels, people wondered who would be next to challenge the streak. The streak was a bigger deal now than ever before as HBK sacrificed his career to try to beat it. It was starting to feel like it was impossible to beat the streak. Triple H was the next one to step up to the challenge as he was Michael's best friend and wanted to finish the job his friend ended his career for. The match was no holds barred and complete chaos right off the jump. Undertaker hit three tombstones and Triple H hit three pedigrees, but both men refused to stay down. There were moments where these two used weapons to brutalize each other as they decided to go extreme to stand out from the Michaels-Taker series of matches. The Phenom got Triple H to pass out to the Hells Gate, but this was the first time he wasn't able to leave Wrestlemania on his own two feet. 

This was the point where it became more apparent to fans and to the WWE themselves that Undertaker had never lost at Wrestlemania. It was Ric Flair's first Mania after returning to the company in 2001; his last Wrestlemania match was in 1992. Flair spent years back in WCW until the doors closed and wasn't the same Flair he was during his first WWE run lacking in self-confidence. The Undertaker personally chose to work with Flair when giving the option and they had a pretty personal rivalry leading up to the match where Undertaker tested Flair's patience, attacking both his best friend Arn Anderson and his son David Flair. The match was an awesome brawl between two veterans and sometimes gets overshadowed because it was on the same card as Rock-Hogan. The Nature Boy bled in vintage Flair style and the Arn Anderson run in with the Double A Spinebuster for an incredibly close near fall was a memorable moment. Undertaker succeeded to give us another great Mania match for a second year in a row. Undertaker visibly counted to ten with his fingers, signaling his tenth victory, and everyone realized the streak we had on our hands.

Randy Orton was the Legend Killer and the Undertaker was a legend with a legendary streak to be killed. Randy Orton was directionless after his feud with his former mentor Triple H and things just weren't clicking with him as a babyface. He had won and lost the World Championship, but still had to prove himself as a singles competitor outside of Evolution. When Wrestlemania came around, he RKO'd his on-screen girlfriend Stacy Keibler and made his intentions clear that he wanted to test his luck against The Phenom at Wrestlemania thus turning heel again. He came closer than anyone else up to this point and there were rumours that Orton was highly considered to beat the streak too. The match was excellent and kept us on the edge of our seats. Orton struck a RKO out of nowhere for a near fall but it took one tombstone out of nowhere to seal the deal for the Deadman. Orton still got over huge due to his performance and the two continued to feud later in 2005.

This match definitely should have been the main event of Wrestlemania 23. It had been a long time since Undertaker had another standout match against a big man on the grandest stage. The last big man matches that stood out were against Diesel and Kane in the 90s. It had also been a decade since The Undertaker competed for the World Championship at Wrestlemania. These two exceeded expectations and tore the house down in the middle of the show. Undertaker brought the best out of Batista and Batista reminded us that he was a force to reckon with. The crowd was engaged in the match the entire time and rightfully so as these two went all out. They made us believe that Batista could have ended the streak and he would have been a solid choice to do so in 2007, but by the end of the year the Undertaker put over Batista multiple times, further establishing him as a star.

I think a lot of us look at this match negatively because we know how CM Punk felt about it. Punk just had a historic 434 day WWE Championship reign and I think a lot of us wanted to see him walk into the main event of Wrestlemania as champion, rather than Rock-Cena 2 needing to be a championship match. I also think Punk should have been involved in the main event, or better yet, Punk could have still defended the WWE Championship against the Undertaker in another streak versus streak match as Punk would have been champion for nearly 500 days. They worked hard to get us invested in the build-up and Paul Bearer's unfortunate passing happened around the same time, so the company incorporated that into the storyline as well. Punk was purposely disrespectful about the death of the Deadman's fallen father figure and former manager. This fired up Taker to avenge him. In the end they had a solid match and told a fantastic story. I was rooting for Punk to end the streak here because I felt like he earned it. Regardless, he carried Undertaker to one of his last great in-ring Wrestlemania matches. If this was Punk's last Wrestlemania appearance, it was a great way to go out.

It was dubbed the "End of an Era" and it was going to take place inside of the devil's structure: Hell in a Cell. The build up of this match started three years prior when Shawn Michaels first challenged the Undertaker at Wrestlemania. Therefore, since Triple H, Undertaker and even Michaels (we like to pretend he never came out of retirement though) all wrestled again after this. I like to think the tagline stood for this four year story between these three men coming to an end, rather than this being the end because they were all officially riding off in the sunset or their era being a dying breed. 

This time around the Phenom wanted to face The Game again since he was unable to walk out of their last match on his own. Taker felt like he won the battle but not the war. Shawn Michaels being special referee added even more drama to the match because he had to choose between helping his best friend and fighting that selfishness of not wanting anyone to accomplish what he couldn't by ending the Undertaker's streak. The match was a dramatic epic where the story made the match better rather than the in-ring action alone. Michaels reacted after all of the major spots made up for the times Triple H and Undertaker spent laying on the mat. I don't think the streak was ever in more jeopardy than it was here, but the Undertaker redeemed himself. To really cap off this four year story arc, the three men walked out together sharing a memorable moment on top of the stage in front of the sold out crowd.

Most sequels never live up to the original, inside and outside of the squared circle, but this one did. Although the fans wanted Undertaker-Michaels 2, I don't think people really expected it to be as good as the first round. But it actually was. This time Shawn Michaels didn't come into the match as confident as he did the first time with the advantage of knowing that the Undertaker had never beaten him. He was distraught over his loss the year before as believed he was so close to ending the streak. Michaels wanted nothing more but to try to face the Undertaker again at Wrestlemania that he was willing to put his career on the line. At this point, if he couldn't beat the Deadman at Wrestlemania he had no career, due to achieving everything else he wanted. The two legends gave us a great match where the HeartBreak Kid fought with everything he had to try to beat The Phenom, but he still fell victim to the Tombstone. This match held a lot more of an emotional weight compared to the first one. Many of us knew Shawn Michaels was heading towards retirement and the result of this match was inevitable, but they still had a terrific match.

This was the best Undertaker Wrestlemania match during his "American Badass" biker run. He only had three matches under that character but this was the one I enjoyed the most. It is also my favourite Undertaker-Triple H match because both legends were in their prime, although Triple H was still the younger guy facing off against the seasoned veteran. However, as far as match quality, due to their abilities in the ring at a younger age and the overall entertainment factor, this match was the total package. It helps that it was in front of the hot Houston crowd on the best Wrestlemania card of all-time. The two entered the feud due to them having a mutual dislike for each other. Triple H claimed to have beaten everyone in the past two years but Undertaker reminded him that he had never beat him, but was willing to make Triple H famous. They had never had a singles match on PPV until this match. They brawled all over the arena through the electric crowd with Triple H trying to do anything to steal a win from The Deadman. The Game also took a huge bump off a camera tower which stood out to me as a kid. Triple H's attempts to out smart Taker failed time and time again. The Deadman stood tall again proving why this was still his yard to a young and confident Triple H, while further growing his Wrestlemania legacy.

This masterpiece is considered one of the greatest matches of all time. By 2009, Shawn Michaels and Undertaker had not faced each other in over a decade, even though they’d been in the same company for all these years. Prior to this match, The Undertaker had never beaten Shawn Michales in singles action. That footnote led Shawn Michaels to be extremely arrogant and confident that he could end the Undertaker's undefeated Wrestlemania streak. Michaels always brought his A-game to the grandest stage of them all, which helped him gain the nickname of "Mr. Wrestlemania." These two always put on bangers and had great chemistry. They were both legends in the game already at this point and very self assured in their own skills due to their years of experience. The entrances to the match told their own story as Shawn Michaels came down from the heavens under a white light, while the Undertaker rose from the depths of hell in the darkness. This match was full of near falls and false finishes, which were still pretty rare at this time in 2009 so they had us all off the edge of our seats. Nobody was able to follow this match and I honestly only remember this show for this match. HBK got caught with a Tombstone when attempting a moonsault, allowing the Undertaker to finally defeat Michaels while keeping his undefeated streak intact. This match was not only flawless but led the foundation for the next three Wrestlemania events. It was arguably the greatest Wrestlemania match of all time, but definitely the best match for these two legends.