My 11 Favourite Matches of The Undertaker

For many years, whenever Wrestlemania season rolled around the biggest question on everyone’s minds wasn’t who would be fighting for the company’s world titles, but who would get the prestigious honour of fighting The Undertaker. A wrestler who has stood the test of time like no other, The Undertaker has wrestled for so long in so many different styles that his mere presence on a card draws more hype than any championship match ever could.

I’ve talked a bit before about how important The Undertaker is to me as a wrestling fan, so as you can imagine I’ve watched a hell of a lot of his matches over the years and it’s safe to say that many of them are among my favourite matches ever. His in-ring ability may have waned somewhat in recent years but that doesn’t stop me getting incredibly excited at the prospect of him stepping in the ring once again, especially since we never really know which time will be his last.

With yet another huge bout set for Wrestlemania 36 in a few weeks against AJ Styles, I thought it’d be a good time to look back at the best of what The Undertaker has offered us, over the years.

11 – vs Brock Lesnar – Wrestlemania 30

Ok, we’ve got to address the elephant in the room with this one, which is quite simply that the actual makeup of this match was awful. Taker, unfortunately, suffered a concussion early on in the match and it left Brock having to carry a bit of dead weight in the ring for a while until Undertaker was able to gather his surroundings enough to form a barely passable match.

HOWEVER

That’s not what matters about this match, what matters about this match is the finish and the moments immediately following it. The Undertaker’s Wrestlemania undefeated streak (aka “The Streak”) was inarguably the greatest draw in modern Wrestlemania history. Once the numbers got up to heights like 13 matches and 13 wins, every year The Undertaker’s Wrestlemania match become an absolutely huge deal. The unmatched aura of a man who’s genuinely undefeatable combined with the consistently brilliant match quality (as we’ll soon discuss on this list) brought The Undertaker’s legacy to such a height that we thought it never could (and many thought, never should) end.

And then it ended.

Many people have spoken on this and I perhaps can’t quite do justice to just how monumental of a moment this was. Several people who witnessed the event live have spoken of the atmosphere of pure disbelief and tragedy in the crowd and said that there is simply no comparison to the feel in the building during the moments following the ending of The Streak. It was a rare moment of genuine shock from the wrestling fanbase, with a feeling that I don’t believe will ever be replicated in wrestling during our lifetimes.

But like I said, the match itself was the drizzling shits, so 11th is the highest it can go.

10 – vs CM Punk – Wrestlemania 29

When people think back on The Undertaker’s run of incredible matches through the late 2000s and early 2010s, this match often gets left off of that list and I think that is a huge disservice to the brilliant match these two put forth.

In the build to this match, Punk put forth what I think is some of his best heel work ever. It played off the real-life death of The Undertaker’s former manager Paul Bearer in a way that I don’t think went too far, even if it was uncomfortable for some. This carried over into the match too and having Heyman sitting on the sidelines, playing along with Punk’s every taunt was just fantastic. There felt like there was a real animosity between these two and it brought us some brilliant moments that capture the essence of what a good Streak match is all about because we’re all so sure that there’s no way The Undertaker’s going to lose, that it’s actually very easy to make us believe he might.

This match also holds a lot of personal weight for me too, as it was the first match I’ve ever watched the whole way through. If you want the full story on that, then I’ve talked about it before but there’s a good chance that if I’d seen a match that wasn’t as good as this one, I wouldn’t have stuck around to become the opinion spewing nerd I am today, which I’m sure would be a great loss to the world…right?….riiight?

9 – vs Brock Lesnar – Hell in a Cell 2015
(Hell in a Cell)

This match stands out for me more because of how surprised I was that it ended up being so good.

Going into this match, Lesnar & Taker had already fought a few months previously at Summerslam and the match was…ok. It was pretty fun and gave us the hilarious visual of Lesnar giving Taker the finger as he passed out, but it was mired by a general slow-pace and very confusing finish that was designed to protect Lesnar but ended up making The Undertaker look like a cheat.

Apparently, the solution to all of these problems was just letting these two guys batter the piss out of each other for twenty minutes in just about every way possible. In the modern era, it’s so rare we get a Hell in a Cell match like this, but it had exactly what the stipulation calls for. There was blood, there were weapons and there was wall to wall violence that ended up being the perfect way to represent the pure hatred between these two competitors.

The action was very exciting too, despite what I had expected, things kept going at a pretty solid pace the whole way through and each weapon spot took the intensity up just a little in order to get the maximum impact out of everything. The finish was great too, with the ring-mat being ripped up and exposing the wooden boards underneath – a spot that remains just uncommon enough to still feel like a big deal – and ultimately, the right man won, capping off a surprisingly brilliant feud that benefitted from some very rare, WWE branded long-term storytelling.

8 – vs The Rock vs Kurt Angle – Vengeance 2002
(WWE Undisputed Championship)

As is probably expected, there aren’t many matches on this list from the “Biker Taker” phase of The Undertaker’s career. Various injuries alongside a generally not very interesting persona or in-ring style meant that a lot of the magic that surrounded The Undertaker was gone during this era and is considered by many fans and critics to be the worst era of his career, so this match is very much the exception, not the rule.

The story going into this match was very hot indeed, mostly just consisting of the three men involved in this match slowly escalating the violence in order to bring the hype for this match up to a fever pitch. This carried over into the match, particularly between The Rock and The Undertaker, who spent a lot of time trying to destroy each other throughout this match. As it stood, Angle slipped into his role perfectly for this match. Angle standing there trying to get the attention of The Undertaker and The Rock as they stare each other down is one of those wrestling gifs that has stood the test of time and it really was indicative of how great Angle was at constantly skimming the line between comedy and serious wrestling.

This match was the kind of car-crash TV that doesn’t always work, but in this case, it really did. All three of these men were constantly colliding in all kinds of ways throughout this match. The action was big move after big move in the best possible way and some classic spots where the men kept stealing each other’s finishers. It doesn’t really tell any kind of grand story, it’s just a pure blast of violence and mayhem from start to finish and stands today and one of the best triple threat matches WWE have ever produced.

7 – vs Batista – Wrestlemania 23
(World Heavyweight Championship)

Alongside his match with CM Punk, this is another one that often gets forgotten when people run down the best Streak matches and I think that’s a massive disservice to the unique style of match these two guys put forward on the night of Wrestlemania 23.

The story of this match is very simple, one big man has a title, one big man wants the title, this leads to the two big men trying to absolutely annihilate each other for fifteen minutes straight and it’s an absolute blast. Seriously, these two guys don’t let up on each other at any point during this match, there’s nothing slow or plodding about it in the slightest. The whole match feels like such an intense fight with big move after big move and some brutal-looking spots through tables and the like.

It also clocks in noticeably shorter than almost all of the other matches on this list, which only helped had to that feeling of intensity. “The Streak” had just about become a thing by this point in time so Batista trying to put The Undertaker down hard and fast was the only possible way he stood a chance of winning, The Undertaker responded in kind and those simple story point carried this whole match to something really entertaining and surprisingly unique for the era in which it took place.

6 – vs Mankind – King of the Ring 1998
(Hell in a Cell)

As much as the focus for this match goes mostly onto Mick Foley (and deservingly so I might add), The Undertaker’s contributions to this match can’t be understated.

We’ve all heard the story of this match a thousand times over so I’ll spare you the details, but despite the match being relatively devoid of any “traditional” wrestling action, it’s guaranteed to keep you involved for its runtime because of the sheer shock and awe of what happens during it. The tension during the moments where they’re on the top of the cell is incredible and no matter how many times you see either of the falls, it never fails to surprise me.

From the points following both of the falls, things continue to go absolutely mental with various people getting involved to tide over the time where no-one was quite sure whether or not Mick Foley had just died and some gruesome looking spots involving thumbtacks just before the finish. Ultimately, all that matters about this match is the absolutely iconic moments it created and almost single-handedly lifted the Hell in a Cell match to legendary status.

5 – vs Shawn Michaels – Badd Blood 1997
(Hell in a Cell)

Oh hello Shawn Michaels, I wonder if we’ll be seeing you again on this list…

I’ve already covered a couple of Hell in a Cell matches on this list, so it only makes sense to go all the way back to the first. Being the first match of it’s kind, this was going to have to leave an impression on the audience and it achieved that in more ways than one through both it’s storytelling and it’s action. During this period of his career, Undertaker was working a much slower, methodical style which worked entirely to this match’s benefit as it meant anytime Michaels got offence in, the crowd started to go nuts for it.

The cell was also used to great effect, for one thing, the atmosphere of the whole thing is so incredibly intimidating and it only gets better when we see some of the archetypal spots that we’ve seen in almost every HIAC since. The whole thing also had quite a claustrophobic feeling to it, something the modern cell has lost with its increase in size but I really enjoyed the cramped feeling of the whole thing, even if Shawn Michaels didn’t appreciate being so close to the cameramen.

It also had one of the truly iconic endings in WWE history as Kane made his debut, tearing the door off of the cell and tombstoning The Undertaker, allowing Michaels to sneak away with the win. The whole set up of that final segment was a wonderful piece of storytelling and made sure that it didn’t feel like a cheap get-out to having Undertaker take the pin. Not only was it a brilliant match in its own right, but it established a new stipulation match as a staple that we still see on a yearly basis today.

4 – vs Edge – Wrestlemania 24

This match is probably the closest one of these matches to the expected modern WWE main-event style, but it’s easily one of the best iterations on that formula I’ve ever seen.

There wasn’t a great deal of complications going into this one. The Undertaker and Edge were yet to collide in a major way during their careers so this felt like a huge clash between two genuine legends of the business. When it comes to what we think of today as the formula for “epic” Streak matches, this had just about all the ingredients and more. Both guys would kick out of a bunch of finishers with a whole bunch of really fun back-and-forth wrestling between the two men.

There were some fun story elements in there too, namely Ryder & Hawkins running down during a referee bump to create some more chaos and really milk the crap out of every near-fall. Then we had the immortal gif of Charles Robinson sprinting his way down the extremely long ramp to count a pinfall that never stops being funny to watch.

As it stands, there isn’t really much more to this match, it’s just some really great action between two really great wrestlers in a spot that both of them absolutely made the most of, with The Undertaker vs Edge feud continuing on for the better part of a year following this and becoming one of the most memorable storylines in Smackdown history. Which is nice.

3 – vs Shawn Michaels – Wrestlemania 25

I know, I know, it’s only third, but hear me out.

In terms of in-ring action, this match is easily head and shoulders above the rest. I could sit here and run down all of the posts but that would honestly do a disservice to how incredibly well built this entire match was, telling its own little story (even though there wasn’t much going into it) and creating one of the most edge-of-your-seat exciting matches I’ve ever watched.

The chemistry between these two competitors is just outstanding. As we saw earlier in this list, these two had been around in WWE for a very long time by this point and every inch of their experience was poured into this match. Even though I knew the outcome when I watched this match for the first time, I still found myself buying into every near fall and each kick out created some wonderful moments following it.

As I’ve said, when it comes to in-ring action alone, this might be the highest quality non-NXT match I’ve ever seen in a WWE ring, but these next two matches have a little something over it that this one doesn’t quite have enough of.

2 – vs Triple H – Wrestlemania 28
(Hell in a Cell)

Story. That’s what makes this match so incredible, the sheer force and strength of its story.

The build to this match alone was enough to get anyone hyped up to see this fight. After Taker & HHH beat each other within an inch of their respective lives the year previous, The Undertaker was desperate for a rematch to prove his victory wasn’t a fluke, but Triple H was too busy being the COO of the company to have any part of it. Invoking Shawn Michaels’ from the previous years was a fantastic move and bringing him in for this match as the special guest referee was a stroke of genius. It tied together the past 3 years of The Undertaker’s Wrestlemania matches into one climactic story of Shawn Michaels and Triple H just trying so desperately to defeat The Undertaker just so they can say they’ve done it.

From a purely wrestling-based standpoint, this match wasn’t quite on the level of many others on this list, but what’s really important is the story surrounding it all, a story that was so masterfully told in the ring as well as in the build-up that it elevated a pretty good match into a transcendent one. I still remember very vividly my feelings in that moment where Michaels super kicked The Undertaker into a Pedigree from Triple H and even though, going into the match I KNEW for a 100% fact that Undertaker was going to win, I still bought into that near-fall and it remains to this day my favourite kickout I’ve ever witnessed.

Even once the match was over, the raw emotion of everyone involved was so incredibly powerful and that image of the three men standing in each other’s arms at the top of the ramp as the “20-0” graphic was behind them is just so amazing that even various awful Saudi Arabia matches can’t cheapen its emotional impact.

1 – vs Shawn Michaels – Wrestlemania 26

Maina 25 had the incredible action, Mania 28 had the incredible story, this match has both.

You take the excellent wrestling contest from the year prior to this one, you mix it up and make it feel fresh and new, then you throw in the added drama of Shawn Michaels’ career – a career that’s spanned almost 2 decades – potentially coming to an end and you’ve got a recipe for what I would argue is the single greatest match in Wrestlemania history.

This match worked in so much from the previous year while still bringing in new spots and new action to weave into the contest. It had such a weight to it as both men were able to predict the other’s movements almost perfectly, seemingly calling back to their previous encounter purely out of spite and emotion. The Undertaker was protecting his undefeated legacy, while Shawn Michales was fighting to keep his living.

As the fight wears on, you can almost feel these two titans of the industry coming to respect one another, as they give each other their absolute best to prove that they deserve to be the winner at the end of it all. This all brings us to yet another incredible moment, where The Undertaker had Michaels dead to rights, but he just won’t stay down. You can see that there’s almost a level of pity on The Undertaker’s face as he stands over Michaels…until Michaels slaps The Undertaker across the face in defiance, telling him that if he’s going to end his career, he better do it properly.

It’s one of those truly rare gems in wrestling where absolutely everything comes together. The story, the action, the finish, the aftermath, it was genuinely perfect and still stands today as The Undertaker’s greatest ever match.

That’s all folks! Thank you very much for taking the time to read this article, please let me know what some of your favourite Undertaker matches are, either in the comments below or on Twitter @10ryawoo. Finally, make sure to come back here this time next week, where I’ll be running down every episode of Doctor Who Series 6!