Ranking The Undertaker’s Wrestlemania Matches

It had to happen. Earlier, this month The Undertaker finally retired.

The man’s career in World Wrestling Entertainment lasted over twenty years and Mark Calloway wrestled a few years in other organizations before that. In his time there, the Undertaker became quite possibly the greatest performer in the company.

The Undertaker had a great gimmick,  had enough presence that he didn’t always need to talk (even though he could), and he was a talented worker who changed with the times.

In many ways, the Undertaker was synonymous with WrestleMania. He had a streak that lasted 21 matches and came back for the event even after he could no longer commit to a full time schedule.

For that reason, let’s countdown every match the Undertaker had at the show of shows. These are ranked from worst to best.

Giant Gonzales – WrestleMania IX

Confession time, I don’t think Wrestlemania IX is as bad as everyone says. I’ll concede it’s not particularly good, but it’s a little better than its reputation suggests.

One of the reasons I bring that up is because I don’t have a lot new to say about this match. It’s not only the worst match on this list, but easily one of the bottom five Taker matches ever.

During his early years, Undertaker spent a lot of time feuding with barely mobile hosses in monster vs. monster matches. Giant Gonzales may have been the worst of the bunch. He couldn’t move, he couldn’t talk, and his costume was downright laughable.

This match is so slow and plodding it could cure insomnia while the finish is one the company likes to gloss over (as they probably like to forget about this match completely). Giant Gonzales and Harvey Whippleman tried to use ether to knock the Undertaker out but the ref busted them.

Yes, this was the only streak match to end in DQ, meaning the Undertaker claimed 20 souls and one doofus who got busted by the ref. If you ever wondered if the Streak was planned or just a coincidence, here’s your answer.

Is there ANYTHING good about this match? Taker’s entrance was pretty cool.

The Big Boss Man – Wrestlemania XV

Here’s another match I have little new to add to.

Wrestlemania XV was loved in its time, but people can now realize it stinks (Don’t feel bad, I used to like it too).

What was wrong with this match? The fact that this match was slow and plodding feel secondary to the now infamous ending where Edge, Christian and Gangrel (The Brood) hanged the Big Boss Man.

The feud was also absurd, with villainous Mr. McMahon looking sympathetic while being tortured by villainous Undertaker. I remember watching that video package as a kid, and thinking “I like the Undertaker and I dislike Vince McMahon, but Taker seems like kind of a jerk.”

And yes, this match is no good.

Taker wrestled very little in early 1999, probably to hide an injury. I’m not sure if it was ring rust or if he was still injured but Taker seemed to forget how to wrestle and was back to slow chokeholds.

There was also a noteworthy botch where handcuffs broke off and an unintentionally hilarious call from Michael Cole where he fretted over a finger being caught in the cell.

King Kong Bundy – Wrestlemania 11

While I have a soft spot for the guy, King Kong Bundy was well past his prime by 1995. The Undertaker was still getting into his groove but also one of the best things in WWF in 1995 (a big fish in a small pond if there ever was one).

Other than an amusing spot where Kama tries to steal Pall Bearer’s urn, there’s little to write home about this match.

Trivia time: This was the first time Vince McMahon mentioned the Undertaker’s undefeated streak… while it was only 3-0 (4-0 after this match).

Big Show/A-Train Wrestlemania XIX

This match has the dubious dishonor of being quite possibly the least interesting match on this list.

Yeah, some of those other matches were worse, but even their badness gave people something to talk about. The worst part is the company was aware of the streak by this point and this was the best they could do?

The only really noteworthy thing is this was supposed to be a tag match, but Nathan Jones was such a bad wrestler they wouldn’t let him in the match. Let that sink in: The company that let Sable have a career wouldn’t let Nathan Jones wrestle.

Still, I rank this one a little higher than the others because it’s neither good enough nor bad enough to really make waves, its biggest crime is being forgettable.

Wrestlemania XIX is one of my favorite events ever, but this is a match I skip.

Jimmy Snuka – WrestleMania VII

Here we go, the match that started it all. The Undertaker’s first Wrestlemania match.

The team behind the scenes probably didn’t realize one of the biggest and most important wrestlers the business would ever see. However, they knew they were building a star.

And that’s the feel of this match: Someone on the way up, beating someone who was on the way out. However, that’s also why this match wasn’t that great: It was someone finding his groove facing someone who was near retirement.

Being the first does make this match noteworthy. So that’s something.

Mark Henry – Wrestlemania 22

This is another match that really isn’t noteworthy.

The company was trying to get Mark Henry over as a monster, but that really didn’t happen until several years later with Mark Henry’s House of Pain gimmick. While I have a certain level of respect for him, Mark Henry was not the best of workers and the Casket Match gimmick was one of the only things that made this match noteworthy.

Sycho Sid – Wrestlemania 13

Honestly, this match isn’t THAT bad. It’s watchable, but that’s it.

The real problem is the fact that this had no business being the main event of the biggest show of the year, a show that featured the stone classic Steven Austin-Bret Hart “I Quit” match. As an upper mid-card match at an “In Your House” event, this may have been fine, but the main event of Wrestlemania? Nah.

It’s common knowledge that this was a last minute replacement for the planned Bret Hart-Shawn Michaels rematch, and boy does this reek of last minute filler. The no DQ stipulation feels like a cheap excuse to add flavor to a heatless match (to be fair, it helped). Plus Hart interfered for no good reason.

Part of the problem was the fact that this match meant extremely little in hindsight. It gave us another Undertaker world title run, but injuries forced Sid off TV for a while, before eventually exiting in June.

Jake “The Snake” Roberts – Wrestlemania VIII

This is one of those matches that isn’t really that great but I still have a soft spot for it.

It’s funny looking at these matches in context and how the streak was created. Like a lot of early matches, this was a case of the company needing to build a star while someone else was on the way out.

In this case, Jake Roberts was about to exit stage left. This match was solid, but probably the most noteworthy part was Taker giving Jake a Tombstone on the floor while Jake tried to steal Paul Bearer’s urn.

Kane – Wrestlemania 20

I wasn’t watching wrestling at the time, so I can’t wax nostalgic for how this felt. This was another match that as is was little to talk about.

Kane and the Undertaker had so many matches by this point (and would have more) that there wasn’t much for them to do. It was basically window dressing for the Undertaker’s return to the Deadman gimmick.

Still, that’s more than can be said about some of the previous matches.

Shane McMahon – Wrestlemania 32

The build for this match was… not good.

Shane McMahon returned after years’ absence in a genuinely mark out moment. Unfortunately, it was all downhill from there. Shane McMahon said he was going to blackmail Vince McMahon with… something so he could gain control of Raw. However, to earn that, Shane had to get past the Undertaker (Holla, holla… sorry I couldn’t resist).

It made no sense that the Undertaker was working for McMahon, and if there’s one person who shouldn’t be the pawn of McMahon, it’s the Undertaker. It’s been reported that Taker and McMahon are good friends behind the scenes, but how many casual viewers know that?

The match itself was watchable but sloppy. There were a lot of botches such as Shane delivering a sloppy Coast-to-coast. This match did feature cool spots such as the Cell breaking and especially Shane diving off the Hell in a Cell. Those moments at least made this match memorable, but it’s still not that great. Both men would do so much better a year later.

Also, Shane ended up controlling Smackdown Live anyway so this match was kind of pointless.

Brock Lesnar – Wrestlemania XXX

And here we have the official end of the Undertaker’s Wrestlemania streak. 21-0 officially became 21-1.

People were so upset and downright shocked when this first happened. This was largely due to Taker and Lesnar having a feud that didn’t have the strongest build.

Also, the match itself was… Look, the word is – Undertaker suffered a concussion early on, and boy is that obvious. Lesnar can normally perform German suplexes that look vicious. Here they looked a little ginger and downright awkward.

or a clash of titans, this match felt slow and the crowd wasn’t that into it. Undertaker finally losing was met with such solemnity you’d think someone actually died.

Kudos to WWE for booking Taker’s first Wrestlemania loss in such a unique way: holding off music, holding off commentary, showing the crowd (including that famous “Just Say Yes” Guy). However, that in conjunction with the underwhelming match turned the whole Lesnar/Taker affair into a downer.

Fortunately, when the Undertaker was in better shape, he came back and had some amazing matches with Lesnar.

Also, I have to give points to this match because it did put Lesnar over in a big way. Allegedly, the company wanted to end the streak for years, and fortunately, they did it with someone they could get mileage out of. Lesnar won the WWE Championship that summer against John Cena and this match help give Lesnar a little more credibility to do that.

Bray Wyatt – Wrestlemania 31

One of the reasons I’m glad I can write these after the Undertaker’s retirement is I can write about these matches in hindsight.

At the time, this match felt pointless. The Undertaker’s streak had been conquered, and he had a throw away match with Bray Wyatt. With no streak, the feud felt like bragging rights over who the “new face of fear” was.

Even if the feud lacked the heat that it needed if Bray were challenging the Streak, Bray’s charisma carried the feud and the match was solid. Considering the previous year, the Undertaker looked like he was dying, solid was a pretty good upgrade.

More importantly, the Undertaker made a minor comeback, feuding with Brock Lesnar and later teaming with Kane in a tag re-match at the 2015 Survivor Series. Taker’s feud with Lesnar was damn good, making 2015 the last great year of the Undertaker, quite an accomplishment considering he hadn’t been a full-timer since 2010 (And 2015 was the year he turned 50).

So for being a “comeback” match of sorts, this match deserves some cred.

Diesel – Wrestlemania 12

I don’t know if this comment will be considered controversial, but I consider the Undertaker a bit of a late bloomer. Ever notice that when WWE puts out those compilation DVDs, very few of the matches are from 1996? That’s one reason the Undertaker is one of the best. The man could have easily coasted off his laurels but instead reinvented himself and improved his style.

For the first time in a while, Taker was going over someone on the way out. This was a fairly solid big man vs. big man match, with memorable spots such as the Undertaker rising up after multiple Jackknife Powerbombs. The Undertaker got the duke after a Tombstone Piledriver and this was a turning point for both men.

Roman Reigns – WrestleMania 33

Here we go, the final showdown, the big one, the final match of one of the most important wrestlers in WWF/E history.

I reviewed this in a full review of Wrestlemania 33 so I’ll do my best not to repeat myself.

One of the hazards about writing about a match this fresh in people’s minds is that it’s hard to say how this match will be seen in hindsight. Roman Reigns has already drawn controversy for being the man who retired the Undertaker. I consider it an acceptable choice and I hope WWE continues parlaying it to make Roman seem more vicious (Seriously, his post-Wrestlemania promo was the promo of his career so far).

I don’t want to give this match points just for being the swan song match of the Undertaker, but that did help. Sadly, Mark Calloway showed his age even if he took some impressive bumps, but (as I said in my review), that was sold as a man doing anything to keep himself alive.

Plus, the lasting image of the Undertaker leaving his ring gear in the middle of the ring and walking away to a chant of “Thank you Taker” was an image that will last longer than any action in the match.

Kane – Wrestlemania 14

This was the first encounter (of many) for Kane and the Undertaker.

The two built a great feud with Kane resurfacing as revenge for being burned alive at a young age by the Undertaker. People lament that the Undertaker was the last of his kind. The reality is he AND KANE were two of the only guys who could do supernatural stuff and still make it look cool.

Undertaker and Kane brought a great clash of the titans to the card at Wrestlemania XIV. The match isn’t perfect – it slows down in spots (like Taker, Kane took a few months to find his groove). However, that is made up for with impressive spots such as Kane leveraging Undertaker’s dive into a table slam.

Even in defeat, Kane established himself as a force to be reckoned with, needing three Tombstone Piledrivers to be vanquished and STILL pummeling Taker after the match.

Randy Orton – Wrestlemania 21

After Randy Orton’s babyface push fizzled out (which I guess is what happens the company gives someone a world title reign just to spite Brock Lesnar for leaving), Orton was quickly returned to his nefarious ways.

While the Undertaker’s streak was often talked about by this point, they were still frequently “grudge matches” where the Undertaker came out victorious. This was the turning point where people started challenging the Undertaker specifically to challenge the vaunted streak. 

A good story was built around this feud with Orton playing the egomaniacal Legend Killer. The previous year, he already had an epic feud with Mick Foley and was taking out many of Taker’s old foes including Jake Roberts. The story was good and the match was fairly solid. Orton displayed he was a star on the rise and Taker showed he still had it with great spots including a chokeslam into an RKO.

Triple H – Wrestlemania 27

I may get wrapped in the mouth for this, but I consider this match a little overrated. I emphasize “A LITTLE overrated” because this match is in fact good. I outranked it over several matches I would, in fact, consider good.

Howeve,r I don’t think it deserved the universal acclaim – including a 4.5-star score from Dave Meltzer (who’s much stricter than I am in his scoring). This was the turning point when the Undertaker started coming out only annually (with few exceptions) to defend his streak. This was also when Triple H would officially become a part timer, focusing more on his backstage role.

The match was good, with some exciting spots – including Triple H actually scoring the Tombstone on the Undertaker (a feat so rarely accomplished, it was practically a victory in itself). We also saw chair spots that proved nobody was above when the new concussion policy when BOTH HHH and Taker received fines for giving chair shots to the head.

The reason I don’t hold this match as highly as some fans is this is the match where we learned one Hunter’s more annoying ticks as a part-timer: padding matches. It felt like after every major bump, Taker and Trips sat around for five minutes.

Ric Flair – Wrestlemania 18

As a no disqualification match, Undertaker and  Ric Flair worked a wild and entertaining bloodbath. Flair showed his love of getting that platinum blonde hair red with blood. This was the Undertaker’s last run as a full-fledged heel (which didn’t take because the Undertaker was just too awesome to boo).

That’s the only downside to this match. The whole feud was built around Taker torturing Flair – attacking his family, attacking Arn Anderson (who interfered in the match). Taker came off like such a bully that we almost wanted to see Flair win.

Undertaker’s victory was still cool, especially when he counted off his ten Wrestlemania victories.

A historical note people tend to forget is that in the storyline, Flair put up his share in the company to face Undertaker, making this the catalyst for the first Brand Extension. Ah, the more things change, the more they stay the same.

Triple H – Wrestlemania 17

Orton may have been the first time people started taking Taker’s streak as a challenge, but this was around the time Taker’s streak was acknowledged, at a then 8-0 record.

It’s funny how this match had a similar build to the matches Taker and Trips would have a decade later – Triple H wanted to face the best in the business and all that was left for him was the Undertaker. The match was pretty good, one of the reasons Wrestlemania X-Seven is held in such high regard. Both men were at the top of their game (Pun not intended).

My only real gripe is the ref bump. Referee Mike Chioda took a bump and was out for an obscenely long time – Whatculture clocked it and TEN MINUTES. Ref bumps are fine for sneaking in a chair shot or something, but it begs the question: Why didn’t they just make this a straight no-DQ match?

The two worked a pretty wild brawl, with some cool spots outside of the ring and Triple H blocking a Last Ride with a sledgehammer. Still a great match though.

Plus we got Motorhead playing “The Game” and Lemmy infamously forgetting the lyrics. I’m guessing Motorhead didn’t play Triple H’s entrance music much at concerts.

Edge – Wrestlemania 24

The Undertaker and Edge certainly had their work cut out for them in this match. They had to follow the entertaining Big Show vs. Floyd Mayweather bout, a solid triple threat match between John Cena, Randy Orton and Triple H. But most importantly, they had to follow Ric Flair’s emotional retirement.

Luckily, they were The Undertaker and Edge. One of wrestling’s great shames is that Edge’s undefeated streak ended unceremoniously the previous year. It’s a shame he didn’t win Money in the Bank in 2007 since he got it anyway. That would have kept Edge’s streak alive for a streak vs. streak match.

The two still had a great story. Edge had screwed the Undertaker out of the world title he rightfully earned the previous year and kept toying with him, costing him a match against Batista at Survivor Series and weaseling out of facing him in a triple threat at Armageddon.

In a level of patience I wish WWE would show these days, Undertaker took a year to finally get his one-on-one match against Edge. It was a classic battle of good vs. evil with Edge playing the despicable heel who did everything he could to weasel out of a loss to the Undertaker.

The match was great, and it told such a great story: Edge was such a heel that people liked to see him lose and the Undertaker was such a great face that fans loved seeing him win. A great match with some surprisingly old school storytelling.

Batista – Wrestlemania 23

At this time, it was well-established that people were challenging the Undertaker for his streak. However, this time the Undertaker was the hunter.

After winning one of the best Royal Rumble matches ever, The Undertaker decided to challenge Batista for his world title. The match and the feud were both brutal. One of the impressive aspects of their feud was that neither man turned heel.

I don’t like how a lot of today’s bookers mistake title chases for actual feuds, but these two told that story right – two men who just wanted the same thing. They wanted the world title and they were willing to do whatever it took to win it. These two worked some intense, brutal matches over that world title and this was the first and one of the best.

Triple H – Wrestlemania 28

Now, this is a match that earns the praise it has received. After Hell in a Cell became a pay per view in 2009, what used to be THE feud-ender began to feel diluted. Some of the PPV-exclusive matches were solid, but more and more and more they were feeling like an annual match instead of the promise of a brutal spectacle (That aforementioned Bossman match being damned).

This was the first time in a while that Hell in a Cell felt like a real spectacle. The match was billed as “The End of an Era”. In hindsight, I’m not sure what that meant since neither man retired. However, it was startling that these were the only stars from the New Generation through the Attitude Era who were still working – exciting, brutal matches no less.

The two told a good story before the match and in the ring. As you can tell by the ranking, they more than topped their previous year’s bout. True, both men worked a lot of their usual spots, but there was less slowdown.

They also worked so many brutal spots that when they did rest, it felt earned. Shawn Michaels’s presence as the guest referee also helped – it added a little extra story with him wanting to back his friend but also respecting Taker’s legacy.

Undertaker got the duke, but with all three men walking away after the match made both of them look like heroes.

CM Punk – Wrestlemania 29

The buildup for this match was controversial, to say the least.

Recently departed Paul Bearer was used as a major part of the feud, with CM Punk and Paul Heyman even scattering Bearer’s ashes. Bearer’s son gave the greenlight, but with what a hellspawn that character has proven to be doesn’t make me feel better.

What DOES make me feel better is Jim Cornette’s claim that Bearer was such a wrestling fan that he would have loved being in the storyline even after his passing.

While Captain Hindsight may argue how wise it was to drop CM Punk from the main event storyline after his year-long WWE Championship run (especially since he may still be in the company), Punk and Taker still had a classic match (the only real classic at the middling event).

CM Punk was the first guy to challenge the streak that was neither HBK nor HHH since 2008 and the first real bad guy Taker faced in a while. When CM Punk touted that he was one of the best and he wasn’t kidding.

Meanwhile, the Undertaker was in such good shape that considered a part-time comeback and even wrestled a few TV matches (including a Smackdown match against Dean Ambrose). It was a great match, and we got Living Colour to perform “Cult of Personality” to boot.

Shawn Michaels – Wrestlemania 25

With a title like this, I don’t think it was a question that Taker’s two matches against Shawn Michaels would be the top two. The question is how I’d rank them. Honestly, I can understand making the argument for either one being the best. However, I’ll explain mine.

While many fans saw this match coming, it was a prime example of WWE going with an obvious idea because it was the right idea. Shawn Michaels and The Undertaker were two best of the best (if not the two best) in the business. In a way, that’s how the build was – Shawn Michaels wanted to face the best and be the one who conquered the fabled streak, even playing mind games by donning white clothes.

The match itself was everything we dreamed it to be (and then some). There were hardly any wasted moments and both men kicked out of seemingly every big move and escaped every finisher (leading to a classic face from the Undertaker).

There is only one demerit for this match: That botch. For the uninformed, The Undertaker performed an impressive dive out of the ring, only for Michaels to push a cameraman (Sim Snuka) into the way as a human shield. Snuka failed to catch him, and the Undertaker landed right on his head.

Watching this live was genuinely frightening: The Undertaker laid dormant for so long I was worried we experienced another Over the Edge situation. Luckily, he was still alive (and wrestled for several more years). In a way, it added a little drama to the match, with Michaels being willing to win on countout and Taker saving himself in just the nick of time.

However, even with the benefit of hindsight, this one botch slows the momentum down. However, it still is one of the Undertaker’s best matches and one of Mania’s best matches.

Shawn Michaels – Wrestlemania 26

Before I joined Pop Culture Pipe Bomb, I wrote a series of articles ranking the best main events of Wrestlemania period. This was the runner up and best non-world title match.

After the titanic match, the two had the previous year, a re-match felt inevitable. And they had to work hard to match that, let alone top it. For starters, the story was even better. They built off Shawn Michaels wanting to challenge the Undertaker’s streak, going so far as to cost him the World Heavyweight title and most importantly putting his own career on the line.

At the time, the suspense was unbearable: They wouldn’t really end the streak! Shawn Michaels isn’t really going to retire! Who’s going to win?

A no disqualification stipulation was added, and probably for the better. As good as both guys were, a different stipulation gave them new cards to play with. The two worked a brilliant match without just copying the previous one. Some of the best spots included Shawn Michaels’s moonsault onto the table and the final moments. Shawn slapped the Undertaker and provoked him to finish him off. Undertaker followed through with one of the coolest Tombstone Piledrivers.

It was as good of a final match HBK could hope for and one of the best matches in both men’s careers.

So there’s my list: Feel free to share your thoughts and rankings.

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