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!
The 15 Best Undertaker Matches of All Time, Ranked
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
The Undertaker (c) vs. Mankind
WWF One Night Only 1997 - 09/20/97
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
14. The Undertaker vs. Ric Flair
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)
12. The Undertaker vs. Triple H
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 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)
9. The Undertaker vs. Edge (c)
WWE WrestleMania XXIV - 03/30/08 (World Heavyweight Championship)
8. The Undertaker (c) vs. Bret Hart
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)
6. The Undertaker vs. Triple H
WWE WrestleMania XXVIII - 04/01/12 (Hell in a Cell Match)
5. The Undertaker (c) vs. The Rock vs. Kurt Angle
WWE Vengeance 2002 - 07/21/02 (Triple Threat Match for the WWE Undisputed Championship)
4. The Undertaker vs. Shawn Michaels
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)
2. The Undertaker vs. Shawn Michaels
WWE WrestleMania XXVI - 03/28/10 (No Disqualification, Streak vs. Career Match)
1. The Undertaker vs. Shawn Michaels
WWE WrestleMania 25 - 04/05/09
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