Ranking The Undertaker’s Wrestlemania matches

25 matches. 23-2. The most incredible record in Wrestlemania history. And whilst The Streak may be behind us, we can still look back on an array of matches and memories that The Phenom has produced on the grandest stage of them all. So here is my personal rankings and reviews of all of The Undertaker’s Wrestlemania matches, ranked from worst to best. Enjoy!

25. Big Boss Man (Hell in a Cell match); Wrestlemania 15 (1999) = 0* (ZERO STARS)

‘Things can only get better’ as the phrase goes (trust me they do… eventually…) but we start off with a real DUD! So this match saw The Undertaker, representing his Ministry of Darkness faction, facing the Big Boss Man, of Vince McMahon’s Corporation, in a Hell in a Cell match. All sounds good right? Wrong! The match itself was sub-standard to say the least, but nobody remembers that as the aftermath was something that made me feel physically sick watching it. After Taker had won the match The Brood (Gangrel, Edge and Christian) ascended from the rafters of the arena and landed on top of the Cell, they then broke the roof of the cell and slid a NOOSE through the gap they had made, and then The Undertaker proceeded to HANG Big Boss Man as Taker’s manager Paul Bearer pressed a nearby button that raised the cell from the ground. So yes indeed, at WRESTLEMANIA a man was left hanging from a noose like something from some vile historical image. It was absolutely horrific and how it was even remotely acceptable even nearly 20 years ago is beyond me. Sickening.

24. Giant Gonzalez; Wrestlemania 9 (1993) = ¼*

Wrestlemania 9 is widely acknowledged as the worst Wrestlemania in history. So that should tell you all you need to know about a match between THE UNDERTAKER and an 8 foot tall man in a full muscle-ridden, fur-covered body suit. The Undertaker has down the years been lumped with a number of ‘monsters’ that WWE have wanted to push as big stars by having them take on their top guy soon after arrival, but Giant Gonzalez may be the most unbelievable and ridiculous of them all. The finish came when Gonzalez covered Undertaker’s face with a chloroform-covered cloth, and the referee waved off the match awarding the win to Taker by disqualification. 7 minutes and 33 seconds of misery.

23. King Kong Bundy; Wrestlemania 11 (1995) = 1 ½*

A match is never going to be good when it is the secondary focus to another story that is being told. And this match was all about the prized possession of The Undertaker; The Urn. The manager of King Kong Bundy, The Million Dollar Man Ted DiBiase, had taken possession of the Urn from Paul Bearer previously only for Taker to take it back during the match and return it to Bearer. That was until Kama (aka The Godfather) came and took it back. Anyway Bundy was on top for most of the match, until the finish came with Taker hitting a scoop slam on the giant Bundy, before a flying Clothesline was enough to get the win.

22. Jimmy Snuka; Wrestlemania 7 (1991) = 1 ½*

The first match of The Undertaker’s incredible Wrestlemania career was also the win that saw him take ‘The Phenom’ moniker from his ‘Superfly’ opponent. Taker punished Snuka en-route to a dominant win in less than 5 minutes in what would prove to be the first of many on the grandest stage.

21. Mark Henry (Casket Match); Wrestlemania 22 (2006) = 1 ½*

This was the zenith of what would be the peak years of both men’s career. A month prior ‘The World’s Strongest Man’ had cost Undertaker the World Heavyweight Championship, this eventually led to the first and currently only Casket Match on the grand stage of Wrestlemania. Henry demonstrated his power early on, Taker responded with a plethora of typically-hard strikes, and he would win the match by following up an amazing dive over the ropes to Henry on the outside (something which would be a re-occurring high spot for The Deadman in his Wrestlemania matches down the years) by rolling him into the ring, Tombstone Piledriver and then Taker rolled Henry into the casket before shutting the lid and extending his record to an impressive 14-0 at Wrestlemania.

20. Jake Roberts; Wrestlemania 8 (1992) = 1 ¾*

The ahead-of-his-time Roberts was the lamb to the slaughter here, designed to get the relatively new to the WWE scene Undertaker over by having him beat a big name on the biggest stage. And he did just that; Roberts would hit his finishing DDT (back when a ddt was a legitimate finisher) for the second time in the match before going to the outside to go after Taker’s manager Paul Bearer. However he would suffer a Tombstone Piledriver on the outside of the ring, eventually allowing The Undertaker to claim his second Wrestlemania victory in convincing fashion.

19. Sycho Sid (No Disqualifications Match for the WWE Championship); Wrestlemania 13 (1997) = 1 ¾*

A match that is more remembered for the fact the main event of Wrestlemania 13 was supposed to be a rematch of the previous year’s classic between Bret Hart and Shawn Michaels saw The Undertaker take on the WWE Champion Sycho Sid (I don’t know how he was champion either) whilst the ‘injured’ former champion Shawn Michaels sat ringside at the commentary table. Bret Hart came out before the match and cut a promo on all 3 men (he was in-hindsight so clearly legitimately pissed off with HBK’s ‘injury’) and he was involved in the finish to as he distracted Sid long enough to allow The Undertaker to hit the Tombstone Piledriver to get the win. This match was awful because Sycho Sid was one of the worst main eventers of all time, and had it not been for the fact The Undertaker won the WWE Championship in the main event of Wrestlemania this match would be even further down the list for sure.

18. A-Train & Big Show (Handicap Match); Wrestlemania 19 (2003) = 2 ½*

This was supposed to see Taker team up with the physically impressive Nathan Jones in a tag team match, but Jones was unable to take part after an attack earlier in the show by both Big Show & A-Train (the real life reason is apparently Jones was taken out of the match due to concerns about how inexperienced he was in the ring still and not wanting to put him in such a big match so early in his career). A Limp Bizkit live performance of Undertaker’s entrance was one of many highlights of what was a great Wrestlemania. Although not one of the best matches on the show it still saw Taker hold his own against 2 huge opponents. The aforementioned Nathan Jones would though make an appearance, as a Spinkick in the crowd on the Big Show and then on A-Train (how this didn’t result in a DQ I don’t know but oh well) would allow for Taker to Tombstone A-Train back in the ring for the win.

17. Kane 1; Wrestlemania 14 (1998) = 2 1/2*

One of the longest running (still being used 20 years later) stories in WWE history had its opening contest in the unholy showdown between The Deadman and his newly-arrived brother. A few months in and Kane was already one of the most interesting and dominant characters we had ever seen. He would continue his dominance in this match before FINALLY succumbing to a 3rd Tombstone Piledriver from Taker for the win. Although Kane kicked out at 3 and beatdown his brother after the match, it was The Phenom who picked up the victory.

16. Diesel; Wrestlemania 12 (1996) = 2 1/2*

2 very powerful and very aggressive strikers did battle in an even contest. The cocky Diesel thinking he had the match in the bag, before being beaten after a Chokeslam followed by a Tombstone. Nice of Diesel to do the job shortly before he went to chase the coin in WCW. We didn’t hear much of him after that………..

15. Shane McMahon (Hell in a Cell Match); Wrestlemania 32 (2016) = 2 ½*

How do you try and save ‘the biggest Wrestlemania of all time’? You throw in your legend and put him in a giant cell against an authority figure we haven’t seen on TV in 6 years! Of course you do… In a match where Shane was fighting for control of Raw and The Undertaker was needing to win else he’d never compete at a Wrestlemania ever again. Going in to this match it was widely expected to be a one spot match, and indeed it certainly was. Shane climbed to the top of the cell and attempted to elbow drop Taker through the announce table, but Taker moved and Shane went through the table instead. He’d soon after suffer a Tombstone as Taker claimed the win. This was entertaining for sure, a technical masterclass it was not, and it was THIRTY MINUTES long. So you make your own mind up…

14. Roman Reigns (No Holds Barred Match); Wrestlemania 33 (2017) = 2 ½*

I have watched thousands of matches in my time as a pro wrestling fan, but this was the one I was most uncomfortable watching. My hero The Undertaker (whom it transpired was carrying an injury going into the match) was far from his peak, in the main event of my favourite Wrestlemania of all time against the man of the moment (who by stark contrast to his legendary opponent was in absolutely peak physical shape) Roman Reigns. And whilst this will be remembered for the lamented 2nd consecutive coronation with fireworks and all of the Big Dog at Wrestlemania and also the ceremonial laying in the ring of The Undertaker’s gear, the match itself was much less physically appeasing. Storytelling it was great, the old Lion fighting the younger Lion in a battle for supremacy, but just having to endure Undertaker (kayfabe or not) take an absolute beating for ¾s of this match was almost unbearable. A grand total of FIVE Spears later, along with a plethora of Superman Punches and chair shots later, notably prompting Roman to tell Taker to “stay down”, he eventually took mercy on The Deadman and rendered him just his second Wrestlemania loss that until very recently looked to be his last in-ring outing.

13. Kane 2, Wrestlemania 20 (2004) = 2 ¾*

The second match between the Brothers of Destruction on the grandest stage of them all saw The Undertaker return after a nearly 5 month absence (after losing a buried alive match at the previous Survivor series to Mr McMahon as a result of interference from Kane). This Undertaker though was different to the one we had seen before this, as with Paul Bearer by his side The American Badass gimmick was discarded and The Deadman returned instead at Madison Square Garden to take revenge on his brother. One of the all-time great Wrestlemania pre-match video packages and subsequent entrances proceeded a relatively short victory for The Undertaker after a Tombstone. And with that the greatest era of this legendary career had begun.

12. Bray Wyatt, Wrestlemania 31 (2015) = 2 ¾*

In his first appearance since losing his legendary Streak 12 months prior, The Undertaker returned to take on the self-proclaimed ‘new face of fear’ Bray Wyatt. Wyatt had for the entire 2 month build to this showdown been calling out The Deadman, questioning his power and mystique now that his streak had gone. In the end Taker proved it was still ‘his yard’ after winning the penultimate match of that years Mania in what was a wonderfully told story between a legend and a current-day superstar wanting trying to take his ‘lord of darkness’ title. A 2nd Tombstone Piledriver, after getting out of a potential Sister Abigail, was enough to take Taker’s record to 22-1.

11. Brock Lesnar; Wrestlemania 30 (2014) = 3*

The match that ended with the most famous moment in WWE of this past 20 years or so, one of the most famous moments in Wrestlemania, WWE and all of Pro-Wrestling history. The end of The Streak. “a 3rd F5 to The Undertaker… Brock Lesnar, into the cover, hooks the leg, The Streak… is over” called Michael Cole, as the crowd in the Mercedes-Benz Arena and everyone watching around the world was left absolutely stunned. The unthinkable had happened. The Beast Incarnate had delivered such a beating to Taker that the physically aggressive, shoot-looking style of offence had actually caused Taker to sustain a serious concussion during the early part of the match (albeit the actual moment was no such fault of Brock’s I should make that clear). It did though mean Lesnar had to take control of the large majority of the match, and that Taker was unable to fully take in the emotional and shocked reaction of the crowd after the match. The ovation he received became secondary to the concerns about his condition, as he stumbled out of the entrance-way and collapsed after the match once he got backstage. He was immediately rushed to hospital for check-ups and was accompanied by Vince McMahon himself. It was the first and only time Vince McMahon had left a Wrestlemania early, which just shows how high a regard Undertaker is held in. Always one to want to give back, this was the ultimate sacrifice. The most prized possession in all of pro-wrestling, The Streak, now belonged to Brock Lesnar.

10. Ric Flair (No Disqualifications Match): Wrestlemania 18 (2002) = 3*

This was the first Wrestlemania in which the former WCW stars were given the chance to shine on the Wrestlemania stage. It’s amazing to think that this match was half way down the card but this was a very unique event, as was this match. Flair bled almost from the start in typcially prefusive fashion, and the personal rivalry that had led to the match continued throughout this gruelling contest. But even with the interference of his best friend Arn Anderson (whom hit an exquisite Spinebuster to his opponent) to try and help him, Flair would eventually succumb to a Tombstone. And with that The Undertaker’s Wrestlemania winning streak was in to double figures.

9. Triple H 1: Wrestlemania 17 (2001) = 3*

This match featured a brawl through the crowd, a live performance by Motorhead, the debut of the American Badass Biker persona of Taker’s at Wrestlemania, a very peronal build up… there was a lot going on! Without being a technical masterclass (that’s still to come) this was an entertaining enough match, the finish saw the heel-ish Triple H be beaten by the Last Ride in the semi-main event of the most beloved Wrestlemania of all time. So not too bad I’d say.

8. Randy Orton: Wrestlemania 21 (2005) = 3 1/2*

It was highly appropriate that the first time ‘The Streak’ was specifically challenged, it was by none other than the ‘Legend Killer’. And Orton himself has since gone on to credit The Undertaker for helping him with this feud and elevating him to that next level. A very admirable match that included interference from Randy’s Hall of Fame Dad & a kick out at 2 after an RKO came to an end when Orton attempted a Tombstone Piledriver of his own… only for Taker to reverse it and hit the move himself for the win…… and we never heard much of Randy Orton again in WWE……

7. Batista (World Heavyweight Championship); Wrestlemania 23 (2007) = 4*

After The Undertaker had finally won his first Royal Rumble match, he went on to challenge Batista and so began one of the all time great series of matches across 2007. But the first is usually the best and this was the case here. It SHOULD have been the main event that year, instead this classic had to make do with the mid card spot. Crowd were enthralled throughout, eventually exploding with joy when Taker finally hit the Tombstone to win the big gold belt for the first time. Fabulous stuff all round.

6. CM Punk; Wrestlemania 29 = 4 1/2*

In a match that’s build up centred around the mocking of the recent passing of The Undertaker’s former manager Paul Bearer, one of the modern day greats carried one of the all time legends to a Wrestlemania classic. Punk (and most fans) would argue he should’ve been in the title match that year but nonetheless he made this match just as special. His mocking and imitations would eventually come back to haunt him as Taker would reverse a Tombstone attempt from Punk to hit his move himself for the win. The final match of the streak, and one of the best too.

5. Triple H 2 (No Holds Barred Match); Wrestlemania 27 (2011) = 4 1/2*

In the lead up to this one, Triple H vowed to do what his best friend (Shawn Michaels) could not; end The Streak. He could not. But in his attempt to he helped deliver an incredible match. Back and forth all the way through, chair shots, finishers hit and nearfalls for both, ended when Taker had the Hell’s Gate submission locked in. Triple H attempted to use his signature Sledgehammer to break the hold, but the pressure of the move was too much for Triple H to handle. After the match The Undertaker was so worn out he had to be carried out by paramedics. For the first time in his Wrestlemania career, The Undertaker failed to walk out the arena on his own two feet.

4. Edge (World Heavyweight Championship); Wrestlemania 24 (2008) = 4 1/2*

2 of the all time greats, in the main event of Wrestlemania, for the World Heavyweight Championship. Need I say more? This was simply excellent. Great storytelling, great wrestling, great drama. Finish was also great as Edge hit his Spear but was locked into the Hell’s Gate upon coming to the ground. The Rated R Superstar eventually succumbing to Taker’s new move, which eventually came to be a story in itself, and for the 2nd year in a row; Undertaker walked out of Wrestlemania with the big gold belt.

3. Shawn Michaels 2 (Streak vs Career); Wrestlemania 26 (2010) = 4 1/2*

Coming 12 months after their first Mania meeting, HBK’s one primary goal turned in to an obsession in the build up. As after Taker initially rejected his demand for a rematch, a failed attempt to win the Royal Rumble would leave a continually spiralling Michaels to cost The Undertaker the World Heavyweight Championship. This was indeed enough to persuade Taker to do a rematch, but only if Michaels put his career on the line. And so how do you follow a classic? With another one! A wonderfully told story had its conclusion when an exhausted yet defiant Michaels slapped Taker, and was punished with a huge, jumping Tombstone to keep the Streak alive, and to give Shawn Michaels the ending of his career that it warranted.

2. Triple H 3 (Hell in a Cell match with special guest referee Shawn Michaels); Wrestlemania 28 (2012) = 5*

‘The End of an Era’ was how this was billed. Indeed it was. 2 legends doing a match neither may ever come close to replicating ever again. This match had everything! Half an hour of sheer excellence. I cannot speak highly enough of it. Widely regarded as the best cell match ever, some even call it the best WWE match ever! The Tombstone would give Undertaker his 20th Mania win but this was more than just a match. The iconic image of Taker, Triple H and Michaels stood on the rampway after the match as they soak in the crowd admiration, and the sheer magnitude of what they just produced is something even your most emotionless WWE fan will surely begin to get teary eyed at. About as close to perfection as you could get in a WWE match… but not quite…

1. Shawn Michaels 1; Wrestlemania 25 (2009) = 5*

What can I say about this match? You knew this was going to be number 1 right? When I began to put together this list I was sure about only 1 thing, that this would be number 1. It’s my favourite WWE match of all time. It’s the best match in the history of Wrestlemania. It’s 2 of the best ever putting on an absolute masterclass. I could write 10000 words on this match and it wouldn’t be enough words to explain how perfect it was. Please watch this match asap. I loved it as a 13 year old, I absolutely adore it aged 22. Thank you for everything Undertaker. Thank you for being the most amazing performer in Wrestlemania history. And alongside ‘Mr Wrestlemania’ thank you for putting on my favourite ever match.

Josh.

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