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Ranking all 25 of The Undertaker’s WrestleMania matches.
On the November 19th, 1990 taping of Superstars, 25 year-old Mark Calaway debuted in the then WWF under the name of Kane The Undertaker. Just three days later, and with the Kane removed from his name, The Undertaker made his pay per view debut at Survivor Series joining Ted DiBiase’s “Million Dollar Team” in victory over Bret Hart’s “Dream Team”. And although he would get counted out in this match, it was very clear to many spectators and critics that not only was The Undertaker over, he had the look of a future superstar.
Over the course of the next of the next 25 plus years, “The Deadman” would go on to win seven world championships, six tag titles, and a Royal Rumble while firmly cementing himself as one of the greatest superstars in the history of the company. He’d go on to main event 58 pay per views which places him third all time in that category, and that number includes four WrestleMania main events.
Beginning at WrestleMania VII in 1991, The Undertaker would go on a run of epic proportions known more formally as “The Streak”, which saw him win a staggering 21 straight Mania matches. In what has become one of the greatest accomplishments in wrestling history, The Undertaker and WrestlMmania have almost become synonymous.
But what were his best Mania bouts? How about his worst? Ahead we countdown all of The Undertaker’s WrestleMwrestania matches from worst to first.
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25. Giant Gonzalez – WrestleMania IX
As impressive and distinguished as this list is, there are undoubtedly a few duds. And Taker’s match with the 7’6 Giant Gonzalez at WrestleMania IX was exactly that. The former El Gigante in the WCW, Gonzalez came to the WWF and things fell apart almost immediately. Donning a body suit that gave him large splotches of fur and fake muscular physique, the company thought that he would be perfect fodder for a guy in Taker that they knew was destined for big things. It was only his third WrestleMania but it was already clear that “The Deadman” was a future world title contender as evidenced by his 6-day title reign in 1991 and his successful baby face turn in early 1992.
So by the time WrestleMania IX rolled around The Undertaker had spent the previous year defeating most superstars in his wake. And in dire need to protect Bret Hart and Hulk Hogan from the hard-charging Deadman, he was put in a series of matches against guys that looked unstoppable. Gonzalez may have looked the part, but he was a train wreck in the ring and his seven and a half minutes inside of one with one of the best wrestlers of all time was a microcosm of that. It would be the only match out of the 25 that did not have a definitive pinfall or submission as Gonzalez was disqualified for using chloroform. Because you know, even though you’re a foot taller and 150 pounds heavier, you definitely need to bring a chemically induced rag to the ring.
This mess would be followed up with a rematch at SummerSlam later that year and two months after that, Gonzalez was out of the company. Sure, it was another Mania notch for Taker but for the most part, a giant waste of time for all involved.
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24. A-Train & Big Show – WrestleMania XIX
Much like The Giant Gonzalez debacle, Taker’s WrestleMania XIX match was also highly unsuccessful due to the lack of talent involved. But this time it wasn’t “The Deadman’s” opponents that lacked talent. The Big Show and A-Train are fine professional wrestlers, but it was actually the person that was supposed tag with Taker that night in Seattle that wasn’t up to snuff. And so not up to snuff that his potential partner, Nathan Jones, didn’t even make it to the ring until the closing seconds of the bout.
Yes, this was a really strange one. Quick history on Nathan Jones and his tenure with the WWE. Jones, an Australian, had a very interesting life before coming to the states and joining the company. A multiple felon by his own admission, Jones had spent the ages of 18 until 25 behind bars for a series of armed robberies. Throw in the fact that he was an admitted steroid user and mental patient and you’d figure that Vince and his buddies would stay far away from Jones. But his size and look were apparently too much for the WWE to pass up and they took a flier on him. Because hey, what’s the worst that could happen?
Well surprisingly the worst thing that happened was that Jones was horrific in the ring. The company tried to work an angle of him being Taker’s protege and the two were then booked for this match at Mania. However, on the road to the “Show of Shows” the company realized that Jones couldn’t wrestle his way out of a paper bag and arranged an angle to keep him out of the ring that night as his opponents attacked him backstage. This left Taker on his own against two guys with a combined weight of over 700 pounds. The match was a dud. And not even the sloppy run-in that prompted Taker’s victory by Jones could save it. What a surprise.
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23. Jimmy Snuka – WrestleMania VII
Look, everyone loves originals. Superman I, Godfather I, the first Mom on The Fresh Prince of Bel-Air, the list goes on an on. Unfortunately for “The Streak”, it’s original is extremely lackluster. Just five months after his pay per view debut at Survivor Series in November, Taker was booked to face Jimmy Snuka at WrestleMania VII. Let’s not take anything away from “Superfly”. The guy was an absolute legend and is responsible for a number of iconic moments in pro wrestling history. But by 1991 when he would run into The Undertaker in Los Angeles, Snuka was 48 years old and his best days were clearly behind him. And that was on full display as Taker dispatched the Fiji native in just four minutes and twenty seconds via Tombstone.
Now, if you want to look for a silver lining in this one, Taker’s win over Snuka is actually the one that propelled him into the limelight. Shortly after this glorified squash match, Taker would embark on a feud with The Ultimate Warrior and by years end would get a taste of the WWF Championship when he beat Hulk Hogan at Survivor Series.
So yes, the match that made Taker 1-0 in what became one of the most iconic runs in professional wrestling history began with a 260 second walk in the park for The Deadman. Luckily for wrestling fans, things would get much tougher.
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22. King Kong Bundy – WrestleMania XI
After an unsuccessful WWF Championship opportunity against Yokozuna at the 1994 Royal Rumble, Taker spent the next seven months on the shelf allowing a back injury to heal. In his absence, Ted DiBiasi, the leader of the Million Dollar Corporation stable, brought in his own imposter Undertaker. That summer, Taker returned and in one of the most underwhelming SummerSlam main events in history, laid waste to the faux Deadman.
With just how badly that angle went over, most figured that his feud with Dibiasi’s clan would be over. But that was unfortunately far from the case. The program spilled all the way into 1995 and resulted in a match at WrestleMania XI. So who from that clan would go on to face The Undertaker at such a marquee event? How about Bam Bam Bigelow? Nope. He was absurdly booked to be in the main event against former NFL player Lawrence Taylor that night. How about Irwin R. Schyster? No again. They’d already wrestled at the pay per view before Mania. How about Kama? That was being saved for SummerSlam. Tatanka? Well, there was no reasoning behind him being overlooked.
This left King Kong Bundy, who by far had his biggest moment in a wrestling ring nine years earlier when he main evented WrestleMania II in a steel cage against Hulk Hogan, to take the inevitable beating. Six minutes and thirty-six seconds later and it was all over for The Walking Condominium and Taker was 4-0 at Mania. Unfortunately he’d be stuck in this program through the summer, but just two years after this win, The Deadman would finally capture his second world title.
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21. Jake Roberts – WrestleMania VIII
Three years before the 6 minute and 36 second destruction of Bundy, Taker battled Jake Roberts at WM VIII, and believe it or not, he defeated “The Snake” in that exact same amount of time. The match itself wasn’t much better than the bout with Bundy which was disappointing. With two supremely talented superstars such as Taker and Roberts, most feel that this should have been a bit better. But although the match was underwhelming, it was an important turning point in the career of The Deadman because it marked the first time that he would turn baby face and the fans support of him grew rapidly.
Just about two months before this installment of WrestleMania, Roberts attempted to assault Randy Savage’s wife, Elizabeth, with a steel chair. Taker intervened and stopped Roberts, and the turn in character was warmly accepted by the WWE universe. This led to their bout at Mania in Indianapolis and although Roberts had his moments including two of his huge patented DDT’s, Taker got the better of him after a tombstone on the floor. The loss sent Roberts packing as he wouldn’t be seen in the company for another four years.
As much as this match failed to live up to expectations, it introduced a different side to “The Deadman” one that he would use to move up the ranks and eventually become one of the greatest superstars in company history. With only his second Mania win in his pocket, it was still very early on for Taker. But one thing was very clear after this match, his star was rising and then some.
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20. Mark Henry – WrestleMania 22
For as quickly and lazily this match with Henry at WM22 was thrown together, it’s no wonder it gets such a low ranking here. This was the second WrestleMania that “The Streak” was a factor as Randy Orton had first breached the subject a year earlier at WM21. But unlike the year before, the build up to Taker/Henry paled in comparison to that of the program with Orton. Taker had just returned to the company at the Royal Rumble after about a month off and challenged then World Heayweight Champion, Kurt Angle at February’s No Way Out show. After being unsuccessful in that quest, he had another shot at Angle mere weeks before WM22 but Mark Henry, for what ever reason, cost him that match.
So what could’ve been a championship match at Mania with Angle, suddenly became a casket match versus Henry. Henry’s only real explanation for wanting the match was so he could be the man to beat The Streak which at that point was at 13 wins. The company went ahead with Rey Mysterio, fresh off a star-making performance at the Royal Rumble to challenge successfully for the world title later that night.
There was nothing inherently wrong with this match against Henry, it just lacked energy. Nobody truthfully believed that “The World’s Strongest Man” was going to win this match and end Taker’s Mania run which was just starting to really mean something. And no offense to Henry, but he’s not the most exciting in-ring performer the company has ever seen. He has limitations, and that was obvious as Taker locked him in the casket in just over nine minutes after fighting off Henry in a match that was essentially over before it even started.
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19. The Big Bossman – WrestleMania XV
So this match does have a bit of a historical presence but that’s about the only reason it ranks as high as it does. And true, at #19 that’s not all that great, but for how much of a snoozefest this turned out to be, #19 is generous. This match versus The Big Bossman at WM XV was the first ever Hell In A Cell match in WrestleMania history. And why is that important? Well some of The Undertaker’s greatest moments of his career have come inside the HIAC. The 1997 match against Shawn Michaels at Badd Blood, the 1998 massacre at The King of the Ring against Mankind, and his wars with Batista, Brock Lesnar, CM Punk, and Edge, highlight Taker’s resume inside the cell. Taker stepping into this type of match alone was worth the price of admission.
But unfortunately only one person brought their A-game on this night in Philadelphia, and it was not the Bossman. Locked in a war with The Corporation, The Undertaker’s Ministry of Darkness was looking to take over the company. There were some very intriguing options from Shane McMahon’s group to face Taker at that year’s Mania. The Rock, Triple H, Ken Shamrock, and The Big Show were members at that time and an HIAC match between any of them may have been a good idea. But for some reason, he drew The Corporation’s bodyguard and muscle, The Big Bossman.
It took Taker less than 10 minutes to dispatch his over-matched opponent running his Mania record to 8-0. But things got even worse (or better depending on who you ask) when with the help of The Brood, Taker strung up The Bossman to the cage and hung him in effigy. Sure, this was The Attitude Era, but essentially murdering a guy during the biggest show of the year was a bit much. And considering that Bossman was back on TV a week later, it may the whole thing seem useless and poorly thought out.
So yes, the event itself was interesting. But the match was not very good.
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18. Bray Wyatt – WrestleMania 31
This idea, on paper at least, had a lot of potential. “The New Face of Fear” taking on “The Deadman” had a really nice ring to it. So when after the 2015 Royal Rumble, Bray Wyatt began his quest to secure a match with The Undertaker, the potential for this match had WWE fans stirring with anticipation. Wyatt had spent the previous 18 months getting over as he battled the likes of Kane, Daniel Bryan, and CM Punk while also establishing himself as one of the more interesting characters the WWE had seen in some time. His wacky, cryptic promos and guru-like control over his Wyatt Family faction was one of the most entertaining programs in the WWE for the better part of two years. This looked to be a huge opportunity for the young star.
But there were some problems. For one, the booking was very one-sided. Wyatt spent weeks cutting promos on Taker but there really wasn’t much a response from The Deadman other than an acceptance of challenge. Because of this, the story line got boring fast and by the time the match happened, any momentum it may have had out of the gates was then non-existent. Also factor in that Taker had finally lost at Mania for the first time a year earlier to Brock Lesnar. Did anyone really believe that he’d lose two in a row?
So the match itself went down that night in Santa Clara and the foregone conclusion nature of it reared it’s ugly head. Other than Taker’s entrance, the crowd was not invested and the 15 minutes that Taker and Bray spent in the ring seemed like little consequence. Taker moved to 22-1 at Mania and Wyatt went back to the drawing board which saw him win a world title a couple of years later. This was not a terrible match or story line at all, but it is most likely The Streak’s most wasted opportunity.
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17. Diesel – WrestleMania XII
The Undertaker/Diesel match at WrestleMania XII is far from a mat wrestling classic. After all, we’re talking about two near 7-footers going head to head and let’s be even more honest, Diesel didn’t exactly have a very diverse wrestling playbook. He relied on elbows, a sidewalk slam, a big boot, and a jacknife powerbomb. But where Diesel excelled, and always did, was his ability, whether baby face or heel, to get over with the crowd. That was the case when he was Shawn Michaels bodyguard, it was the case during his 358 day World Championship run for the majority of the previous year before this match, and it was absolutely the case during the buildup to this showdown with The Undertaker.
Diesel, who had been a baby face after mercifully saving all of us from any more of a Bob Backlund title run in November of 1994, quickly turned heel after losing his championship to Bret Hart at the 1995 Survivor Series. His contempt for Hart and any future title defense got him in The Undertaker’s cross-hairs as he twice interfered in title matches involving The Deadman. This led to one of Taker’s most iconic moments as he, during the championship rematch between Hart and Diesel at In Your House: Rage in the Cage one month before Mania, came up through the mat and pulled Diesel underneath with him seemingly into the abyss.
This all culminated in this match from WM XII which was a solid, if unspectacular match. Both guys did what they had to do and when it was all over, Taker was still undefeated and well on his way to finally capturing another world title.
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16. & 15. Kane – WrestleMania XIV & XX
So let’s go ahead and get these two out of the way together because let’s face it, as much time as the WWE has spent telling the Kane/Undertaker story over the years, their matches are never anything special. And that includes both their Mania bouts. True, they’re two athletic big guys who should be able to produce better together than they have over the years, but the problem may just be that Kane, the “brother” of the Undertaker, modeled his style to that of Taker and therefore their matches, no matter how complex the WWE wants to make the stipulations, pretty one-dimensional.
In the Summer of 1997, Taker’s now former manager, Paul Bearer, began to make reference to a mythical half brother of The Deadman and warned him that he would arrive soon. That day occurred on October of that year when Kane appeared at the Badd Blood pay per view and tombstoned his brother after a tremendous HIAC match with Shawn Michaels. Kane would once again hinder Taker from defeating Michaels, this time at the Royal Rumble in a casket match. After The Undertaker was locked in the casket, Kane set it ablaze. Taker returned two months later and finally went head to head with “The Big Red Machine” at Wrestlemania XIV. The duo did what was expected, put on a perfectly reasonable match that saw Taker get his revenge and victory.
Fast forward to six years later and the brothers were at it again and in the buildup basically followed the same formula as their first go around. Kane interfered during Taker’s Buried Alive match with Shane McMahon at the 2003 Survivor Series culminating in another match at WM 20. This time the match lasted less than seven minutes and seemed like filler between what was two tremendous world championship matches that night in New York City.
Great long term story. Underwhelming in-ring action. Nothing more, nothing less.
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14. Sycho Sid – WrestleMania 13
After five WrestleMania’s that gave him a 5-0 record, and nearly seven years being seen as one of the most dominant superstars within the company, The Undertaker finally got his WrestleMania main event. Not only was the main event due, but his shot at a world championship without getting screwed over by a relative or a rival was even further overdue. As much popularity and fanfare as The Deadman always seemed get, he could never climb that mountain. But that all changed at the Rosemont Horizon in Rosemont, Illinois, the sight of WrestleMania 13.
Now, once again, was this one of Taker’s best in-ring matches? No. In fact, he and Sid put on a bit of a snoozer. Truthfully, it was one of the more underwhelming Mania main events of all time. And throw in the fact that Bret Hart interfered making in an unclean finish, and there was plenty left to be desired about this match. But that did not negate the fact that Taker was finally on top, a spot he deserved long before this night.
In what would be the second of his six world title runs in the company, Taker would dominate the company over the course of four and a half months as fought off the likes of Steve Austin, Mankind, Triple H, Farooq, and Vader before ultimately dropping the belt to Bret Hart at SummerSlam. But not only did this match and title win entrench the Deadman as a top star, it kept him there, as he was at or near the main event scene in the company for the next 15-plus years.
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13. Roman Reigns – WrestleMania 33
If this list were entitled “Undertaker Matches That Enraged The Most Fans”, this match with Reigns at WM33 might be number one. But the fact of the matter is that for how many people the result of this main event angered, it was a pretty solid bout. And if Taker was going to walk away from the ring after it was over, and by the way he left his coat and hat in the middle of the ring it appeared that he would, then this would be a half decent way to do it. That part all appears moot at this point considering that all signs are pointing at a Taker/John Cena showdown at WM34, but had that not been the case, there are worse ways that The Deadman could’ve retired.
As mentioned, the match was decent. A heck of a lot better than Reigns’ main event the year before against Triple H although the crowd was pretty much the same level of against him as that match. But he and Taker took it to each other and outside of a few sloppy moments, the match was hard-hitting and felt real. It was a smartly booked match as well. If this was going to be Taker’s last hurrah, the fact that Reigns had to conjure everything he had inside of him and deliver spear after spear to finish him off made a lot of sense.
Taker taking his second WrestleMania loss to a guy like Reigns was never going to be a popular decision. Reigns has been an arguably more polarizing character than John Cena ever was in just the last three years and an honor like defeating The Deadman at an event that he has forever immortalized was tough to swallow. But history is history and the WWE will have live with it’s mistakes. But for the most part, these two men did what they had to do in Orlando that night.
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12. Shane McMahon – WrestleMania 32
Just one year before his second Mania loss to a 3-time WWE Champion and two years after his first, that time to a 5-time WWE Champion, The Undertaker went to battle inside Hell In A Cell against a guy in Shane McMahon who’s hardly wrestled more than 100 matches in his entire career. Before this match, Shane actually hadn’t been inside the squared circle for a wrestling match in almost seven years. Was there a chance that a guy in his position could walk into WrestleMania and hand Taker only his second loss in just 24 chances? Even with the caveat that Shane would take over RAW with a victory, the chances were still pretty slim.
But even with that logic in place, Shane and Taker went out there in front of over 100,000 fans in Arlington, Texas and put on a match that was befitting their current capabilities. The problem? Their current capabilities, especially Shane, couldn’t carry the match in a way that would have been befitting to a Taker Mania match. It was a bit of a dud, honestly. Shane was never the best worker on the planet and to compound that, his seven year hiatus made even more rusty than normal. His striking looked flat out ridiculous in this match. And for Taker, well at 51 years old at that time, there was only so much carrying he could do.
What this match will be forever remembered for however, and a big reason it made it as high as it did on this list, was McMahon’s suicidal-like jump from the top of the cell. Some people might just call it another McMahon high-spot, something he’s been known for over the years, but in this case it was an example of how far a man is willing to go to try and gain a win over Taker at WrestleMania. When it’s all said and done, it’s a feat that so few will ever be able to say they accomplished and Shane proved he was willing to try anything to be immortalized. So yes, the match didn’t live up to expectations, but it still created yet another massive Mania moment that involved The Deadman.
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11. Brock Lesnar – WrestleMania 30
Truth be told, this should’ve been better. More special is maybe the better way to put it. When Brock Lesnar was booked to face Taker at WM 30, I think it was safe to say that most people figured that this would be a Taker victory. Because really, what would’ve been the point of Lesnar breaking the 21-0 streak? Many figured that this honor would eventually be bestowed upon a young, upcoming talent that would help further the business into the future. Lesnar, a part-timer at that point in time and already a 3-time WWE World Champion, really didn’t have much to gain in winning other than cementing his already pretty padded legacy.
So it made things all the more shocking when the referees hand counted to three in New Orleans with Lesnar covering Taker. It was really a stunning development, one that made many wonder if the pinfall were an accident and that the The Deadman was maybe injured. But as things hashed over the next few weeks, it became apparent that this was no accident and that the company had in fact decided to give Lesnar the honor of snapping The Streak. Looking back, he quite possibly did many of us a favor because if it was not going to be “The Beast Incarnate” it undoubtedly would’ve been Roman Reigns. You think the fan reaction to Reigns owning Taker’s second loss was bad? Fans may have rioted if he won the first.
But with all things being equal, up until the finish of Taker/Lesnar, the match was pretty bland. It was a 20-plus minutes of back and forth striking, submission attempts with no rationale, and of course, since it was a Lesnar match, a litany of suplexes. It was just a bit of a plodder.
However, with the historical significance of The Streak being ended, this is a very important part to the overall story.
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10. Ric Flair – WrestleMania X-8
At the 1991 Survivor Series, Ric Flair, who was brand new to the WWF at that point in time, assisted in The Undertaker’s Championship victory over Hulk Hogan, making Taker the youngest WWF Champ at that time. Over a decade later and with virtually no in-ring contact between Flair and The Deadman, Flair interfered during a match between Taker and The Rock at No Way Out, but this time Flair cost his former cohort the match. Being that this occurred just one month before WrestleMania X-8, most fans began salivating over the prospect of these two getting together on the company’s biggest stage. And after a few weeks of Taker brutalizing Flair and his family, the match was set for The SkyDome.
Now, the fact of the matter is that if this match happened maybe 5-10 years earlier, we probably would’ve gotten an all-time classic. But with Taker at 38 years old and Flair 53, expectations were certainly tempered. And there were definitely some spots where the duo struggled. The match was made as a no disqualification bout and it seemed that was only done to mask the combatants limitations making the violence a bit gratuitous. Plus, for such an iconic match, it took place in the middle of the card, rendering it a bit anti-climactic.
But the good certainly outweighed the bad as the two tore into each other, both men being lacerated along the way. And come on, who didn’t jump out of their seat when “The Enforcer” Arn Anderson interfered and nailed Taker with a brilliant spine-buster? The ending sequence was also nicely done as Taker reverted back to the Tombstone as opposed to The Last Ride to pick up the victory.
Was it perfect? No. But it was certainly befitting for a match on this stage between two of the best to ever lace up the boots.
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9. Randy Orton – WrestleMania 21
As mentioned earlier, this build up and match with Randy Orton at WrestleMania 21 was the first time that Taker’s “Streak” was really factored into the proceedings. Walking into The Staples Center in Los Angeles, The Deadman was officially 12-0 when he took on “The Viper” and the newly 25 year-old Orton made clear his intentions. “The Legend Killer” as he would name himself at that time had already been a world champion, breaking the record for youngest a year earlier when he bested Chris Benoit at the 2004 SummerSlam for the belt. He wanted his newest trophy to be Taker’s Streak. It was the perfect matchup: “Legend vs Legend Killer”, and Orton prepared himself to do anything to make it happen.
The opening minutes of the match were a bit boring with both guys feeling each other out, fearful of each others finishers. But the match picked after about five minutes into their 14-minute affair, and what began slowly picked up and then some as Orton tried time after time for the pin Taker even after simple moves proving his eagerness for the win. And the final moments were a lot of fun as Orton’s dad, “Cowboy” Bob Orton, interfered and drilled Taker with the arm cast that it seems like he’s been wearing for 35 years. Even after that interference and an RKO, Taker would not stay down and he’d eventually reverse Orton’s Tombstone attempt into one of his own to move to 13-0 at Mania.
As important as this win was for Taker and his Mania legacy, it was far more important to the young career of Orton. A young man who was pushed to the moon perhaps a little too early, as evidenced by his failed baby face turn the year before, he used the moment and importance of the match to recharge his career. These two would clash again five months later at SummerSlam where Orton grabbed a victory and then we all know where Orton went from there. 12 more World Championships and flat out iconic status. That may never happened without this WrestleMania match with The Deadman.
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8. Triple H – WrestleMania X-Seven
On September 23, 1997, The Undertaker, in the midst of a feud with Shawn Michaels in the aftermath of an errant chair shot that cost The Deadman the WWF Championship at SummerSlam, took on Michael’s cohort, Triple H, in a quick, two minute singles match on an episode of RAW. And believe it or not, over the course of the next three and a half years, despite both men being at or near the main event scene, the two had not squared off again in a pay per view singles match. The duo decided to change that as they embarked on a personal, violent feud in the weeks leading up to WrestleMania X-Seven. “The Game”, frustrated over not getting a title shot at Mania, got the next best thing in Taker on this night in Houston.
For all of Taker’s Mania matches, this may have been the best brawl. It was booked as a straight up singles match, but about halfway through the encounter, the referee went down, and then stayed down after Taker dropped an elbow on the back of his head. This allowed the two superstars to venture outside the ring and eventually into an elevated production area. And in the spot of the night, Hunter took a massive bump through a table from off of the structure that thrilled the near 70,000 in attendance. And of course, no massive Triple H match would be complete with his trusty sledge-hammmer which he used to bust Taker open once back inside the ring.
The only fault to be found here was the ending. It was far too obvious as to what was going to happen when Triple H was pounding on Taker’s head in the corner in a perfect position for The Last Ride, which is exactly what happened. For a guy dubbed “The Cerebral Assassin”, it was a bit silly for him to fall susceptible to that mistake.
But that aside, this was terrific match that pre-main evented the one of the greatest WWE shows of all time. But believe it or not, Taker and Triple H would do it better at Mania two more times. But we’ll get to that.
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7. Batista – WrestleMania 23
When The Undertaker won the 2007 Royal Rumble, his one and only Rumble win, he had the tall task of deciding which WWE Champion to face at WrestleMania 23. He had the choice between RAW champion, John Cena, or SmackDown Champion, Batista. Being that Taker was always a guy to pick a fight with the biggest guy in the room, he went with “The Animal”, a guy he had very little history with. In fact, before WM23, the two had never squared off in a singles match against each other. And that was a shame, because it became crystal clear very early on in this bout that the two had tremendous chemistry together and Taker would consistently push the much less experienced Batista to new heights, something that helped Batista excel in his career moving forward.
The build up to this match was a lot of fun. Batista began the proceedings with a massive amount of respect for his challenger, but that nice sentiment quickly evaporated after Taker attacked the champion numerous times leading up to this clash. Batista began to fight back and even turned on Taker in an inter-promotional tag match against Cena and Shawn Michaels at No Way Out a month prior.
So the atmosphere was aptly contentious between the two by the time Mania came around and it showed in spades. Taker, although almost five years Batista’s senior, was in tremendous physical shape for this match and he would need it. The two battered each other senseless and as much as Taker wanted Batista’s belt, Batista wanted Taker’s Streak just as much. It was about as hard-hitting as a 16 minute match could be and both men took massive punishment. But of course it was Taker who got the victory to move to 15-0 at Mania, but also snatch up his fifth world title, and his first in over five years.
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6. Triple H – WrestleMania XXVII
Ten years after their first battle, Triple H and Taker would do it again, but this time it wasn’t about status in the company. It wasn’t about who was going to be next in line for a WWE Championship match. And it certainly was not about vengeance or personal grudges. This match was about two things. Each man’s legacy and whether or not Triple H could be the man to end The Streak. For proof of that, look at each man’s activity for that year. “The Game” only wrestled in four televised events in 2011, and they were all pay per views. Taker only wrestled in one, this one. So to say that this was a special event and that both guys had one last thing to prove is an understatement.
Although both guys were clearly past their prime, HHH at 41 years old and Taker at 46, the amount of rest they both had made them both fresh for this No Holds Barred match in Atlanta. And they held nothing back. They broke tables, dented chairs, and took massive bumps. And sure, the amount of finishers that each man, especially Taker, kicked out of was a bit gratuitous. But it was also beautifully poetic as it illustrated both men’s desire to either end or keep The Streak alive.
The ending of the match was nicely done as well as “The Game” went for his trusty sledge-hammer to put away Taker, who’d absorbed a ton of punishment, only to get caught in The Deadman’s Hell’s Gate gogoplata submission which forced a tapout. The match was everything that this type of stage deserved between two of the most successful superstars of generation. But they weren’t done just yet.
credit: wwe.com
5. Triple H – WrestleMania XXVIII
In what would be The Undertaker’s only WrestleMania trilogy, he and “The Game” would go one more time, this time just a year after their second encounter. However, when their match from the year before ended, The Undertaker, due to the massive amount of physical punishment administered by Triple H, was carted away from the match on a stretcher and directly to a hospital for evaluation. In January, just three months before the WM28, Taker returned to the WWE for the first time since that harrowing scene from the Gerogia Dome. Faced with the harsh reality of his aging body yet refusing to accept it, he challenged Hunter again in an attempt to erase the way his performance at WM27 had ended. After refusing for weeks, Triple H, after being goaded not only but Taker but Shawn Michaels as well, accepted the challenge.
And of course, in typical Taker fashion, this had to be a Hell In A Cell match, his bread and butter. But “The Game”, having defeated the likes of Cactus Jack, Chris Jericho, Kevin Nash, and Michaels in this setting, was no stranger to the demonic structure. Add in the caveat that shortly before WrestleMania, it was announced that Michaels, Hunter’s best friend, was going to be the special guest referee, and The Streak suddenly looked to be in a bit of jeopardy. And although things weren’t as personal as the first go around between these two, there was an intensity to the third leg of this trilogy that was palpable.
Much like the first two matches, this one was ultra-violent. But unlike the first two, this match told a tremendous story and some of it revolved around Michaels. HBK, who was so vital the success of The Streak, refused to help Triple H unfairly end it. However, he was thrust into physical action after Taker locked him in The Hell’s Gate, and his ensuing Super Kick almost won “The Game” the match. But after a scintillating final sequence that saw Taker use the sledge-hammer and a Tombstone to end things, the roller coaster came to an end.
To cap off such a special match and to provide another incredible Mania moment for all involved, the three men shared an embrace on the ramp. A truly special night in the midst of The Streak.
credit: wwe.com
4. CM Punk – WrestleMania 29
At the 2009 SummerSlam, CM Punk, after defeating Jeff Hardy for the World Heavyweight Championship in the main event, was attacked by The Undertaker. With this attack, Taker, who had been on a four month hiatus before this shocking return, immediately inserted himself into a world title picture that needed some star power. Sure, Punk was a rising superstar in the making having won three world championships in just a little over a year since coming to the main roster from ECW, but he lacked a signature feud that could solidify him as a top draw. This is where The Deadman came in to play. Their feud played out into the Fall before Taker ended things and walked away with the belt, but Punk proved he could hang with one of the company’s all time greats, a fact that would help him down the line.
Three and a half years later these two would link up again, and although the build up to their WM29 match was only about a month long, it was about as personal as any in Taker’s career. The night after Punk’s victory in a fatal 4-way to become Taker’s challenger for Mania, Paul Bearer, The Deadman’s long time manager passed away. And in true Punk fashion, a guy who was never afraid to test the boundaries of good taste, stole Taker’s urn that carried the ashes of Bearer (storyline obviously). And the distaste continued when Punk jumped Taker three weeks before Mania and dumped the remains on him. Yeah, this was going to be good.
But for as much heat as Punk tried to garner before this showdown, the 80,000 plus in Rutherford, New Jersey that night seemed split down the middle. Punk, who’d just before Mania lost the WWE title to The Rock after a 434 day reign specifically so the Mania main event could be a Rock/Cena rematch, had a heavy fan base. So as the two waged war over 22 minutes in what was very easily the best match of the night, Punk’s openness about the lunacy of the main event, made it very likely he’d succumb to Taker.
And succumb he did but it was only after he pushed The Deadman to new levels and reminded everyone why he really did deserve a WrestleMania main event.
credit: wwe.com
3. Edge – WrestleMania XXIV
The Undertaker had a litany of great rivalries throughout his storied career. A few that immediately come to mind are Steve Austin, Kane, Mankind, Bret Hart, Shawn Michaels, the list goes on and on. But potentially the biggest thorn in the side of Taker from 2007 until 2009 was “The Rated R Superstar”, as the two engaged in what of the most underrated feuds in WWE history. It started in May of 2007 when Edge cashed in his MITB contract on Taker during an episode of SmackDown and sent him off TV for about four months. Two months after the return, he picked up where he left off with Edge and the feud lasted all the way until WrestleMania 24.
Being that the Taker/Edge program was by far the most engrossing story line in the company at that time, it was fitting that the duo claimed the main event on this night in Orlando. And like usual, their match did not disappoint. It always seemed like Edge and Taker gelled perfectly together and although this wasn’t the best match in their rivalry, it was very close. It was a smart match too with both men using creative counters to their opponents best moves, indicating that these two knew each other so well at that point, they could telegraph what the other would do next. Edge pulled out all the stops, including interference from his La Familia stablemates, but it was to no avail. After nearly 24 minutes heart-stopping minutes, he tapped to the Hell’s Gate.
This was truly the first match that The Streak looked in serious jeopardy. Edge, already a 4-time World Champion and a top superstar in the company would have been more than worthy of someone who could end vaunted run. And although he’d come up short at WM 24 when Taker took his World Heavyweight Championship, his performance here was the catalyst that would net him seven more word titles in the next three years before his unfortunate retirement.
The Undertaker and The Streak did a lot for many of the superstars who were a part of it. But Edge may have been its biggest recipient.
credit: wwe.com
2. Shawn Michaels – WrestleMania XXVI
Through all the years, wars, title matches, and tribulations, the fact of the matter is that Taker’s two best Mania matches were against Shawn Michaels at WrestleMania’s 25 and 26. This match, the latter of the two and the main event of WM26, was another instant classic between these two, and although it’s not quite as good as what they produced a year earlier, this one is still arguably a top 10 match in WWE history, as well as a top five in the history of WrestleMania.
The Michaels/Taker saga goes back long before 2009, the year of WM25. This feud goes back to the 1997 SummerSlam when Michaels, as special guest referee in Taker’s championship defense against Bret Hart, inadvertently drilled Taker with a chair intended for his sworn enemy, Hart. This cost The Deadman his championship and he set his sights on revenge on Michaels. This led to the first ever Hell In A Cell match two months later between the two men that HBK won after Kane’s debut and interference. It was one of the most violent matches the company had seen up to that point. The two continued their rivalry into 1998 when Michaels defeated Taker at the Royal Rumble to retain the WWF Championship he’d taken from Hart via The Montreal Screwjob the previous November.
Fast forward ten years later and the 2007 Royal Rumble. On that night, Taker would get his one and only Rumble win but it took a battle with Michaels in the final minutes to accomplish the feat. Most didn’t know it then, but this was the ground work for what would be two of the greatest matches in WrestleMania history.
So in the second of their two legendary matches, the two once again pulled out all the stops. Michaels hit Taker with everything he had including Sweet Chin Music. It took a jumping Tombstone from The Deadman to end not only the match but Michaels’ career, as a retirement stipulation was on the line.
Again, not as good as their first match, but this one got the main event, the spot it rightfully deserved.
credit: wwe.com
1. Shawn Michaels – WrestleMania XXV
And here it is. Of all 25 of Taker’s WrestleMania appearances, this match with Michaels still, and most likely always will, reign supreme. The only down side to this match was this it was not the main event of this show. In fact, it was not even the pre-main event. The pre-main event was a halfway decent triple threat match for the World Heavyweight Championship between John Cena, Edge, and The Big Show. The main event was another painfully boring chapter in the Randy Orton/Triple H saga. But to be fair to everyone involved in those two matches, it would’ve been nearly impossible to match what Taker and Michaels did in their bout. It left the 72,000 fans in Houston mentally exhausted and ready to head home after such an epic clash. The next two matches didn’t have a prayer.
There were only a couple of small things that separates this match from the WM26 match a year later. For one, the match played out like a history lesson as Taker employed, in order, all four of his finishers from over the years. The ChokeSlam, Tombstone, Last Ride, and Hell’s Gate were all administered on HBK, none of them finishing in him off. Another thing that set this one apart was Taker’s suicide plancha over the top rope that Michael’s pulled the cameraman in front of. Taker landed directly on his head and to this day that moment goes down in WrestleMania lore. For The Deadman to battle back after such a horrifically bad fall only added to the intrigue of such a legendary battle. It took a second Tombstone, one that only happened after Taker caught Michaels in the middle of a moonsault, one of HBK’s classic maneuvers.
This match set the bar for any WrestleMania match that succeeded it and to this day, nothing compares. The desperation that both men oozed throughout this amazing 31 minutes proved just how important The Streak is to the professional wrestling business and showed that even past their prime, just how incredible the talent of Taker and Michaels really was.
Next: Revisiting The Original Lesnar vs. Reigns Match
Will anything ever compare in terms of WrestleMania again? We’ll have to wait and see. But one thing is for sure: placing two generational type talents in one ring on the biggest stage in professional wrestling will result in utter greatness.