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WWE
By: Elton Jones
Published Nov 13, 2023
History was made at WWF Survivor Series 1990 when one of the greatest gimmicks in professional wrestling was born. With Brother Love as his first manager, Mark Calaway aka The Undertaker slowly strolled down to the ring while his spine-tingling theme music reverberated throughout the Hartford Civic Center. As the crowd looked on, 'Taker destroyed multiple victims with his Tombstone Piledriver and cemented himself as someone to watch. A "Decade of Destruction" followed and even after that, "The Deadman" continued to produce iconic moments and unforgettable matches that locked him in as WWE Hall of Famer. Now that 'Taker has finally hung up his boots, placed his hat to the side, and left behind his trench coat, now's the perfect time to look back on his WWF/E run in the only way we know how - by ranking the 15 best Undertaker matches of all time!
RELATED: John Cena: Best Matches From His Storied Career, Ranked
Honorable Mentions
WWF In Your House 13: Final Four 1997 - 02/16/97
Four Corners Elimination Match for the Vacant WWF Championship
The Undertaker vs. Bret Hart vs. "Stone Cold" Steve Austin vs. Vader
WWF In Your House 14: Revenge of the 'Taker 1997 - 04/20/97
WWF Championship
The Undertaker (c) vs. Mankind
WWF One Night Only 1997 - 09/20/97
WWF Championship
The Undertaker vs. Bret Hart (c)
WWF Vengeance 2001 - 12/09/01
WWF Hardcore Championship
The Undertaker vs. Rob Van Dam (c)
WWE No Mercy 2002 - 10/20/02
Hell in a Cell Match for the WWE Championship
The Undertaker vs. Brock Lesnar (c)
WWE One Night Stand 2008 - 06/01/08
Tables, Ladders, and Chairs Match for the Vacant World Heavyweight Championship
The Undertaker vs. Edge
WWE SummerSlam 2008 - 08/17/08
Hell in a Cell Match
The Undertaker vs. Edge
WWE WrestleMania XXVII - 04/03/11
The Undertaker vs. Triple H
WWE Hell in a Cell 2015 - 10/25/15
Hell in a Cell Match
The Undertaker vs. Brock Lesnar
15. The Undertaker vs. Kane
WWF WrestleMania XIV - 03/29/98
Now I hear what you're saying - this match wasn't exactly an all-timer when it comes to in-ring excellence. But the incredible storyline that built up this highly-anticipated war made this first-time matchup between The Brothers of Destruction one of the biggest highlights of 'Taker's career. The engrossing plot threads behind this one involve Paul Bearer teasing Kane's appearance, Kane finally making his debut during the inaugural Hell in a Cell Match, and Kane pushing 'Taker to the point that his brother went against his wishes of not facing his brother by finally accepting his WrestleMania challenge.
The entrances for this clash of the demonic giants set the mood perfectly for what was to come. Seeing both men stare each other down got set the crowd on fire (no pun intended). Once 'Taker went into attack mode, his game plan started to come undone since his punches had no effect on "The Big Red Machine." For most of the match, Kane walloped his brother with all manner of powerful uppercuts and clubbing blows - he even smashed his back with a set of steel steps on the outside!
When 'Taker finally got the upper hand, he made a huge mistake by flying over the top rope and getting caught in mid-air & slammed right into the announce table. Back in the ring, 'Taker shook off the cobwebs and used everything in his arsenal (punches, clotheslines, a leg drop, a Chokeslam, and three Tombstone Piledrivers) to bring his brother down after a hotly contested encounter. It's always fascinating to look back on how an amazing storyline went a long way toward making the crowd care so much about a match such as this one.
14. The Undertaker vs. Ric Flair
WWE
WWF WrestleMania X8 - 03/17/02 (No Disqualification Match)
Here's another example of another one of the best Undertaker matches lifted up by an engaging storyline. Heading into this one, the heel version of Biker 'Taker made it clear that he wanted Ric Flair in the ring at WrestleMania. Flair denied his request...that is until he brutalized his son David Flair in one of the most vicious and unintentionally funny beatdowns in wrestling history. After witnessing that backstage assault, "Slick Ric" stepped back into the ring to take on one of his toughest opponents to date. Now for those of you who read Flair's autobiography, you all know that his confidence was shot at this time and he didn't know if he could perform at the high level he was always known for beforehand.
Thankfully, Flair showed and proved at WrestleMania X8! This brawl showed just why he holds the title of "Dirtiest Player in the Game" thanks to all the repeated punches, chops, and the less-than-sportsmanlike conduct he put on display here. 'Taker came off like a killer here as he rocked Flair with all manner of punches, big boots, and clotheslines to force the "Nature Boy" to rock a crimson mask. Watching all those crowd cameras flash as 'Taker planted Flair with a superplex is one of the most iconic moments of this match. The same can be said for the shocking return of Arn Anderson, who rocked 'Taker with a sick Spinning Spinebuster!
Flair's constant comebacks had the crowd on edge as they watched him clobber 'Taker with a steel pipe and a random sign while still bleeding all over the place like a stuck pig. Flair's Figure-Four Leglock looked to have the match won at one point, but it was all for naught as 'Taker eventually kept his legendary foe down via a Tombstone Piledriver. This hardcore war between two Hall of Famers is a bloody good time!
13. The Undertaker (c) vs. Jeff Hardy
WWE Raw - 07/01/2002 (Ladder Match for the Undisputed WWE Championship)
When it comes to unforgettable matches that deliver pure emotion that had the crowd crying out for the babyface to prevail, this one immediately springs to mind. That's why it's earned a spot here on this list of the best Undertaker matches. Before 'Taker would go on to defend his Undisputed WWE Championship against The Rock and Kurt Angle simultaneously, he had one last problem to handle - an out-of-nowhere challenge from Jeff Hardy. What really made this match believe that Jeff actually had a chance at winning was the fact this bout was booked as a Ladder Match! The fans in attendance for this show got to enjoy one of the greatest matches in Monday Night Raw history.
The start of this match started off hot as Jeff kicked a ladder right into 'Taker's face and followed that up by launching himself right onto the "Deadman" on the outside. A steel chair shot from Jeff kept him strong for a bit until 'Taker caught Jeff slipping with a clothesline. 'Taker brutalized Jeff with his big-man offense while Jeff pulled off some unorthodox offense with the assistance of a ladder. It's so inspiring to go back and watch Jeff make some desperate comebacks to elicit the most passionate of positive crowd responses every time he does it! The ladder continued to play a huge part in the offense of both men - 'Taker landed a leg drop on Jeff while he was trapped within a ladder, plus things got even crazier when Jeff kicked 'Taker right in the balls and proceeded to bounce off a ladder to splash him soon after.
Jeff had everyone hop out of their seats when it actually looked as if was going to unhook the title during the closing moments of this match. Even after the beating he took from front to back, Jeff still had it in him to do the unthinkable. Sadly, 'Taker crushed his and everyone's dream by chokeslamming Jeff off of the ladder & grabbing his title. This match is a hell of an emotional rollercoaster!
12. The Undertaker vs. Triple H
WWE
WWF WrestleMania X-Seven - 04/01/01
It's so wild how WWE went out of its way to completely ignore this match during the buildup to 'Taker and Triple H's clash at WrestleMania XXVII. That's simply a crime! Both men produced yet another one of the best Undertaker matches on a card that's regularly referred to as THE best WrestleMania of all time. Biker 'Taker showed up to do "The Game" really dirty after HHH terrorized him in the weeks leading up to this wild encounter. As soon as 'Taker hopped off his bike, the shit truly hit the fan! Both men clobbered each other for a while until 'Taker punched HHH so hard that he flew onto an announcer's table. Once the action segued into the ring, both men pulled out a host of their signature moves to weaken the other.
The tide truly changed here once HHH threw 'Taker off the top rope as he attempted to pull off his trademark Old School maneuver. HHH then went on to maintain an offensive advantage over 'Taker for a good while. He even went as far as trying to destroy 'Taker once and for all with his trusty sledgehammer. Earl Hebner, who reffed this match, took that weapon right out of his hands. But to the shock of everyone, Earl went down for the count soon after when HHH got catapulted into him for an epic ref bump. A Chokeslam looked to have HHH down and out once a second ref showed up to count the pin, but HHH kicked out!
A second ref bump thanks to 'Taker elbow dropping that aforementioned ref soon led to some chaotic action that occurs within the crowd. While fighting on top of a scaffold, HHH smashed 'Taker with repeated chair shots while the crowd roared on. But he soon paid for his transgressions once 'Taker got to his feet to Chokeslam HHH to a pair of mats below. Back in the ring, two crowd-popping moments took place that made this match worth placing here - a Sledgehammer smash to 'Taker's head that got HHH out of position for The Last Ride and 'Taker finally pulling off that move by countering HHH's 10 punches in the counter. 'Taker prevailed here in the first 'Mania bout to be contested between him and HHH!
11. The Undertaker vs. CM Punk
WWE
WWE WrestleMania 29 - 04/07/13
While it was disappointing to see CM Punk lose a match to John Cena that took away his chance at facing The Rock for the WWE Championship at this show, fans were pleased with the consolation prize that is this match. After Punk disrespected the hell out of 'Taker by mocking Paul Bearer and his urn by spilling the deceased manager's "ashes" out of it, everyone knew the "Straight Edge Superstar" was due for the ass-whupping of a lifetime here. After both men hit the ring after their WrestleMania entrances, in-ring greatness ensued. Punk clearly had studied 'Taker's game before they threw hands here as he landed a bunch of strikes and managed to steer clear of his opponent's offense on multiple occasions.
Punk's cockiness eventually got him into trouble as 'Taker tripped him up on the top rope when Punk tried to go for his own version of Old School. 'Taker got his kicks in for a while before Punk took over once again and used enough offense to ground 'Taker & keep him in position for a successfully landed flying elbow drop. Punk looked as if he had the match in the bag until 'Taker for back to his feet and dazed him with a sky-high Chokeslam. As this match wore on, both men made the crowd come alive even more - Punk crashed through 'Taker with a flying elbow drop through the announce table, 'Take landed a Tombstone Piledriver on Punk just mere seconds after getting hit with a Go to Sleep, and Punk cracked 'Taker in the back of the head with an urn to escape The Last Ride!
The epic finish of this bout, in which 'Taker slipped out of another GTS attempt to land a second devastating Tombstone Piledriver, capped off the only match worth rewatching from WrestleMania 29!
10. The Undertaker vs. Batista (c)
WWE WrestleMania 23 - 04/01/07 (World Heavyweight Championship)
Based on the jaw-dropping performances of both men during this WrestleMania classic, it's clear that 'Taker and Batista had a massive chip on their shoulders. WWE thoroughly disrespected their World Heavyweight Championship match smack dab in the middle of the card! Based on that head-scratching decision, it's clearly evident that both men went out there to have the sort of match that has "TOP THAT!" vibes attached to it. As soon as the opening bell rang, Batista cut 'Taker off with a sudden Spear, an assault in the corner, and a clothesline over the top rope. 'Taker shocked "The Animal" by landing on his feet and pulling him out of the ring, but Batista quickly course-corrected and continued beating down his challenger from pillar to post.
Back in the ring, Batista continued having 'Taker on the ropes. Then the tables turned as 'Taker broke out his signature moves, such as that lethal Snake Eyes and Big Boot combo, to wear down the champ. 'Taker then returned the favor to Batista for his outside thrashing tactics by landing an apron leg drop and flying right over the top rope to crash land on his opponent. This big-man war got even more intense as Batista smashed 'Taker through an announce table with a sick Running Powerslam. Once the action returned to the ring, another Spear, a Spinebuster, a Batista Bomb, a Chokeslam, and a Last Ride entered the equation to elicit passionate responses from the crowd as they produced crazy near falls.
'Taker eventually sealed the deal and became the new World Heavyweight Champion after KO'ing Batista with a Tombstone Piledriver. Both men showed and proved that they deserved a higher spot on the 'Mania 23 card with this effort from another one of the best Undertaker matches.
9. The Undertaker vs. Edge (c)
WWE WrestleMania XXIV - 03/30/08 (World Heavyweight Championship)
A year after WrestleMania 23, 'Taker finally got the respect he deserved by being in a World Heavyweight Championship that sat at the top of a WrestleMania card! This time around, he locked horns with the infamous "Rated R Superstar" at his highest levels of sliminess and incomparable heeldom. This match kicked off on a high note as Edge's shoving of 'Taker resulted in him catching the meanest of hands. Edge finally gained some steam when he Speared 'Taker off the ring apron right into the crowd barrier. Edge damaged 'Taker for a bit more until 'Taker gave him a serious case of whiplash when he launched him off the top rope and had him land back first on the outside ring padding. 'Taker wasted no time as he took flight to collapse right on top of Edge!
'Taker practically "owned" Edge for a good while until the champ planted 'Taker back first onto the ring barrier rim and had him fall right into the laps of the front-row fans. As the in-ring action continued, Edge cut off much of 'Taker's signature offense - these moments played into the fact that Edge clearly took note of 'Taker's familiar gameplan and had an answer to many of his finest maneuvers. 'Taker had a shining moment during those exchanges as he kicked Edge right in the face during a Spear attempt and pulled off a Chokeslam as an immediate follow-up! Later on, 'Taker finally landed the Old School and The Last Ride to really put the champ in a bad place.
As this match reached its conclusion, a ref bump came into play when 'Taker cracked the WWE official with an errant boot to the face. Edge's dirty tactics, which saw him kick 'Taker right in the balls and crack him over the head with his title, did nothing but get him a close two-count near fall. Even more madness ensued as another ref sped down the ramp to call the match and Edge's "Edgeheads" interfered on their mentor's behalf. 'Taker got rid of Edge's lackeys, survived a Spear, and finally overcame his foe by tapping him out with a gogoplata submission hold. 'Taker and Edge really did a bang-up job when it came to presenting the World Heavyweight Championship as strongly as possible in the 'Mania XXIV main event.
8. The Undertaker (c) vs. Bret Hart
WWE
WWF SummerSlam 1997 - 08/03/97 (WWF Championship)
Not only do fans point to this match as another one of the best Undertaker matches, but they also tag this encounter as the catalyst for the important events that gave life to the "Attitude Era." Around 1996, 'Taker began breaking out a new version of himself that incorporated a bit more agility and varied moves into this repertoire. That form matched up extremely well with the "Excellence of Execution," who rose to the occasion to face 'Taker for his WWF Championship. To make matters even more enticing for the fans, Shawn Michaels was instituted as the special guest ref while he was in the midst of beefing with "The Hitman."
Once all three men entered the ring, Hart and 'Taker clobbered each other with nasty strikes as "HBK" tried his best to break them and get a sense of normalcy to take over the proceedings. Those attempts failed as the men he was tasked with officiating brutalized each other outside the ring - Bret's back took the brunt of several shoves into the steel ring post by an enranged 'Taker during those exchanges! 'Taker continued brutalizing Bret's weakened back in the ring until Bret took aim at 'Taker's leg to cut down his larger foe. Bret's gameplan, which included a Figure-Four Leg Lock - even when 'Taker broke the hold and left the ring to beat up his former manager Paul Bearer, Bret cut him down once again while Shawn looked on in disgust.
This classic SummerSlam encounter level of mayhem increased as 'Taker clocked Bret's Hart Foundation buddies when they made their presence felt and when 'Taker got super pissed at Shawn for not counting the pinfall for him after he Chokeslammed Bret. As the match wore on, both men broke out their most crucial moves - Bret even smashed 'Taker over the head with a steel chair to gain the advantage! The finish of this match is so damn good - after catching a nice wad of spit from Bret, Shawn mistakenly swung a steel chair into the face of 'Taker. This major error cost 'Taker the title, awarded Bret with WWF's top prize, and left the fans buzzing after witnessing such an excellent WWF Championship clash.
7. The Undertaker vs. Kurt Angle (c)
WWE No Way Out 2006 - 02/19/06 (World Heavyweight Championship)
Ask anyone what really should have the World Heavyweight Championship match contested at WrestleMania 22 instead of the one we ultimately got and they'll point to this hard-hitting bout! Before WWE's "Show of Shows," Angle put up his title against a version of the Deadman that was more in tune with his MMA prowess. With Kurt at the height of his powers and more of a roughneck in the ring, this match shined the spotlight on two WWE legends who embraced their most vicious selves to stay in the fight.
After a few moments of Angle slipping out of 'Taker's deadly grasp, 'Taker finally got ahold of the Olympic Gold Medalist and began going to town on him. Angle finally pulled off a successful counter by dodging 'Taker's boot and planting him with the first of many German Suplexes. This match's high levels of intensity stayed intact as 'Taker revived himself just in time to catch Angle in midair and ram his back right into the steel ring post. 'Taker stayed in control for a hot minute until Angle began taking aim at his leg and tearing up the Deadman's now injured limb. One of the coolest counters of all time went down when Angle caught 'Taker's leg in an Ankle Lock outside the ring when he caught his opponent's leg right out of an apron leg drop!
Angle and 'Taker simply tore into each other with everything but the kitchen sink as their title match wore on - Angle put 'Taker through the announcer's table with an Olympic Slam, Angle flung 'Taker off the top rope with a Belly to Belly Suplex, 'Taker broke out an Ankle Lock with a slick Gogoplata submission counter. After more Ankle Locks, Angle Slams, and a Chokeslam were doled out to increase the crowd's excitement, Angle secured the win with a shocking roll-up win that countered 'Taker's Gogoplata. Here's an example of one of the best Undertaker matches that features the Deadman in his glorious MMA phase.
6. The Undertaker vs. Triple H
WWE WrestleMania XXVIII - 04/01/12 (Hell in a Cell Match)
For wrestling fans who grew up watching 'Taker, HHH, and HBK during their glory days at the height of the 90s and 00s, this "End of an Era" matchup encapsulated the very best of those beloved eras. The fact that it was held inside the Hell in a Cell added an extra sense of importance to this WrestleMania XXVII rematch. This time around, Shawn threw on a referee shirt once again to oversee one of 'Taker and HHH's most important matches. Coming into this bout, the fans had two questions at the front of their minds - is the fix truly in for 'Taker now that HHH's best friend is officiating this match and will "The Streak" really come to an end in the match type that 'Taker made famous?
The fans got both questions answered as this match kicked off and saw both men meet each other in the middle of the ring to swing for the fences. As expected, the action spilled outside the ring and saw 'Taker weaken The Game by flinging him into the steel steps, the cell itself, and even backdrop him right into the mats below them. HHH got back into the fight after DDT'ing 'Taker in the ring, but that winning moment led to a losing one once 'Taker backdropped HHH right off the top of some steel steps! But to everyone's surprise, HHH rose up to plant 'Taker with a Spinebuster right onto those same steel steps!
As this match continued, HBK wore his emotions on his sleeve as he watched one of his greatest rivals and his best friend fight for their lives right in front of him. Then, the fans got to see one of the greatest near falls in wrestling history after HHH slipped out of a Tombstone Piledriver, shoved him right into a Sweet Chin Music, and capitalized by hitting him with a Pedigree...AND ONLY GETTING A TWO-COUNT SOON AFTER! Even after all that, 'Taker willed himself back into fighting shape to bash HHH with a steel chair, clock him in the noggin with a sledgehammer, and finish him with a Tombstone Piledriver to cap off his 'Mania series with HHH with a winning score of 3-0.
5. The Undertaker (c) vs. The Rock vs. Kurt Angle
WWE Vengeance 2002 - 07/21/02 (Triple Threat Match for the WWE Undisputed Championship)
Here's the second instance of Angle popping up in another one of the best Undertaker matches and the first case of The Rock appearing in one. During the summer of 2002, 'Taker's "Booger Red" persona was running wild with the WWE Undisputed Championship around his waist. After previously putting away Hulk Hogan, HHH, and Jeff Hardy, 'Taker was now forced to defend his title against Angle and Rocky at the same damn time for his highly sought-after prize.
This Triple Threat Match is certainly one for the ages, folks! It starts off on a hilarious note that sees Angle get tired of 'Taker and Rocky ignoring him to jaw jack with each other, which leads to Angle getting that attention in the form of dual punches and a swift Clothesline right out of the ring. 'Taker and Rocky went back to focusing on each other for a bit until 'Taker caught a Clothesline of his whole to the outside and got flung into the steel steps by a refreshed Angle. Angle soon took 'Taker's spot in the ring as he and Rocky brought the pain to each other.
Once the action got back into the ring, a serious case of signature/finisher theft kicked in! Rocky laid out 'Taker with a Chokeslam, Rocky locked Angle in his own Ankle Lock, Angle responded by landing a pretty clean Rock Bottom, and 'Taker shocked the world when he executed a picture-perfect Angle Slam on Angle. As this match wore on, all three men stayed in the ring to land their biggest moves and net some serious near-falls. The hot finish brought this multi-man encounter to a satisfying end as Angle looked to have the match won by Angle Slamming 'Taker, only for him to meet his end as turned around to get launched into the air for a final Rock Bottom.
4. The Undertaker vs. Shawn Michaels
WWE
WWF Badd Blood: In Your House 1997 - 10/05/97 (Hell in a Cell Match)
Due to the events of the SummerSlam 1997 main event and the months following it that saw Shawn become the biggest douchebag in the company, 'Taker got the honor of competing in the first HIAC match against the man that screwed him out of retaining his WWF Championship during the summer. Once both men entered the cell, Shawn pleaded for the outside officials to open the main door and give him the freedom he so sorely wanted. But those cries for help didn't mean a thing - 'Taker got his mitts on HBK and did him dirty for much of the opening portion of this match. It's pretty funny to watch Shawn's overselling during this part, too. To be honest, it actually adds to the match instead of taking away from it.
Moments later, 'Taker kept having his way with Shawn by repeatedly flinging him into the cage and clobbering him with stiff punches. In a moment of desperation, Shawn landed a Suicide Dive to 'Taker that shoved the Deadman back first into the cell. HBK finally got a chance to cook 'Taker as he landed a flying elbow drop off the side of the inner cell wall, a flying Clothesline from the ring apron, and used a set of ringside steps to further injure 'Taker's back. Shawn continued to be in control of the match when he used a Piledriver that planted 'Taker's head right into those same ringside steps!
As this match continued, Shawn maintained the upper hand until 'Taker sprung back to life and spooked HBK to the point that he left the HIAC after ringside officials unlocked it to save an injured cameraman. This match entered the greatest of all-time territory as both men got into a legendary brawl on the outside, took their fight to the top of the cell, and ended with 'Taker stomping HBK's hands & forcing him to fall on top of the announce table below him. Back in the ring, 'Taker cracked HBK with a steel chair and looked to have this all wrapped up...then HE came! Kane, who had been teased by Paul Bearer for the longest time before this bout, made his grand debut by ripping the cell door right off its hinges and using 'Taker's own Tombstone Piledriver to KO him long enough for HBK to nab the win.
3. The Undertaker vs. Mankind
WWF King of the Ring 1998 - 06/28/98 (Hell in a Cell Match)
Everyone and their grandmother who watched this match live still speak highly of this Hell in a Cell match. While there may have been better HIAC matches quality-wise, the belief of several fans that existed during the Attitude Era is that this is the quintessential HIAC bout that has never been topped. Mankind is simply a madman for kicking this match off by climbing to the top of the structure, isn't he? A steel chair aided the masked psychopath for a few minutes before 'Taker made history by flinging Mankind right off the top of the cell to the announce table below. An audible gasp could be heard throughout the crowd as they looked on with worried faces while Mankind was tended to by medical officials.
Everyone figured this match was over...but then Mankind blew everyone's minds when he climbed right to the top of the cell to keep this match going! Then another wild moment occurred as 'Taker Chokeclammed Mankind right through the top of the cell to the mat below! With a tooth hanging out of his nose, Mankind continued to brawl with 'Taker inside the cell and around the ring perimeter within it. Mankind pulled off his biggest move up until that point with his signature Piledriver to 'Taker right on top of a chair. The hardcore action that transpires here is still jaw-dropping when you watch it back - Mankind's back got stuck with a whole bunch of thumbtacks when 'Taler dropped him back first onto them first and Chokeslammed him soon after.
After that devastating combination, 'Taker finally put Mankind out of his misery with a Tombstone Piledriver. Even though this HIAC match didn't run that long, it's still remembered for being one of the most violent matches in WWE history and definitely another one of the best Undertaker matches of all time.
2. The Undertaker vs. Shawn Michaels
WWE WrestleMania XXVI - 03/28/10 (No Disqualification, Streak vs. Career Match)
Just one year after stealing the show at WrestleMania 25 (more on that match later!), Shawn had revenge on his mind. For months and months, HBK pleaded with 'Taker for another chance at trying to break the most legendary streak in all of professional wrestling (until it was broken by you-know-who, sadly...). 'Taker denied him on several occasions and eventually paid for that decision - in an act of complete madness, Shawn climbed from underneath the Elimination Chamber and shocked the world by cracking 'Taker with Sweet Chin Music. This shocking moment led to 'Taker losing his World Heavyweight Championship to Chris Jericho, which finally pushed the Deadman to accept HBK's challenge...but only under one condition. If HBK lost, his wrestling career had to come to an end.
When these two legends stepped foot into the ring for their second 'Mania meeting, HBK dipped into his bag of mind games as he used 'Taker's throat-cutting gesture to get into his opponent's head. This clearly angered 'Taker, who proceeded to brutalize HBK most of the starting moments of this matchup. Shawn finally found an opening as he targeted 'Taker's leg and even did further damage to them via a Figure-Four Leg Lock. Things began looking dire for 'Taker, but he changed the losing tides for himself to a winning one when he surprised HBK with a Chokeslam just a few seconds after Shawn pulled off his kip-up taunt! Another crowd-popping moment took place soon after as 'Taker caught HBK in midair on the outside and proceeded to plant him with a Tombstone Piledriver as a follow-up counter!
As this match wore on, both men pulled out all the stops with their best signature moves and finishers. But they just weren't enough to nab the win for their respective users. HBK even got desperate enough to land a Moonsault onto 'Taker while he was laid out on an announce table! Taker woke himself back up in time to counter HBK with followup Chokeslam's and Tombstone Piledrivers, but they still weren't enough to finish Shawn. The epic closing stretch of this bout saw HBK taunt and slap the hell out of 'Taker one last time as he knew his time as an active in-ring competitor was near its end. With one last Tombstone Piledriver, 'Taker ended Shawn's career (until he came back to the ring in 2018, sadly) and added another amazing 'Mania matchup to his all-time career record.
1. The Undertaker vs. Shawn Michaels
WWE WrestleMania 25 - 04/05/09
Without a shadow of a doubt, THIS is the undisputed GOAT when it comes to the best Undertaker matches! A whole generation of wrestlers saw this match play out in its entirety and realized right then & there that they wanted to enter the wrestling business for themselves. 'Taker and HBK came into this match much older yet so much wiser, which led to them putting together a match lifted by strong storytelling and a wonderful pace that kept the fans on the edge of their seats as it played out.
As this match played out during its opening moments, both men showed that they were on equal ground as they tore into each other with their respective strikes and signature submissions. 'Taker eventually screwed up missing an apron leg drop, but he woke himself up back in time to shove Shawn off the way as he tried to land a Moonsault from the top rope! Then one of the scariest moments in wrestling took place when 'Taker missed a Tope Con Hilo and almost landed right on top of his head after wiping out on a nearby cameraman! Back inside the ring, HBK looked to capitalize on a now weakened 'Taker. But this plan ultimately failed as HBK got taken down hard to the mat with a vicious Chokeslam.
'Taker tried going for another Chokeslam to really incapacitate HBK, but Shawn finally woke himself back up to knock 'Taker's hands off of his throat and lay out the Deadman with some Sweet Chin Music! What followed that shocking moment were several slick counters, more successful attempts at both men's respective signature moves & finishers, and an uncharacteristic moment where 'Taker failed to land a top rope flying elbow from the top rope! The incredible end of this match saw 'Taker catch HBK right out of his top rope Moonsault attempt and take the crowd's breath away once again when he ended Shawn with a final Tombstone Piledriver for the win.
Fans refer to this match as the best WrestleMania match, the best Shawn Michaels match, and the bout most deserving of making the top of the list for anyone ranking the best Undertaker matches of all time!
And with that, we've reached the end! Here's hoping you enjoyed every bit of The 15 Best Undertaker Matches of All Time, Ranked!
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