The Spin List: 10 essential Undertaker matches

Jun 22, 2020

IF WrestleMania 36 was indeed the last time The Undertaker will see action, what a career it was.

For 30 years, professional wrestling fans have been treated to countless classics, whether he put on the persona of The Deadman or the American Badass.

That's why it's such a hard task to pinpoint the matches which one can consider as his greatest throughout the The Undertaker's more-than-three-decade career.

Yet here we are, and Spin.ph selected 10 matches The Undertaker had which we believe fans should watch, whether it be through the WWE Network or the clips available on YouTube.

1. The Undertaker vs Shawn Michaels, WrestleMania 25


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This one's a no brainer.

Without question, two of the top performers in history delivered a classic like no other in the 25th edition of the grandest stage of 'em all.

Michaels played mindgames in the buildup and even came to the ring in a white trenchcoat, a stark contrast to The Undertaker's dark persona, as he pulled out all the stops to prove that he's the superior in-ring performer.

This match was also iconic for The Undertaker's gutsy suicide dive which saw him land on a cameraman and almost go head-first to the floor.

Michaels attempted a moonsault to finish the match, but he got caught as The Undertaker executed a Tombstone Piledriver to score the pinfall and hike his unbeaten streak to 17-0.

Was this the greatest match in WWE history? If it's not, we're not sure what is.

2. The Undertaker vs Shawn Michaels (Career vs Streak), WrestleMania 26

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How do you top a classic from just year before?

It was a tough act to follow, yet The Deadman and The Heartbreak Kid did what they could.

Obsessed to redeem himself from a year before, Michaels put his career on the line and fought like a madman, delivering a multitude of Sweet Chin Musics and also landed a moonsault to a prone Undertaker on the announce table.

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It was 24 minutes of heart-stopping action, with big moves after big moves being delivered between two performers who refused to give an inch to their foe.

The Undertaker told Michaels to stay down, yet the latter responded with the throat-slit gesture and slapped the former in the face. The Deadman took it upon himself to finish it for good, nailing a jumping Tombstone Piledriver to end the career of HBK.

3. Shawn Michaels vs The Undertaker (Hell in a Cell match), Badd Blood: In Your House (1997)


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At this point, you may be thinking that this might as well be a list of all the duels between The Undertaker and Shawn Michaels, but hear us out.

This is the first Hell in a Cell match. Probably lost in the in the whole mystique of the stipulation was that this was a no. 1 contender's match for Bret Hart's WWF World Heavyweight Championship.

Michaels, then the European Champion and affiliated with D-Generation X, had to face The Undertaker by himself and tried his best to outpower the bigger man.

Both men climbed to the top of the cell midway through the match which ended with The Undertaker stomping a dangling Michaels on the side of the cage, causing him to crash through the Spanish announce table.

Yet what still keeps this match memorable for a lot of fans was the debut of Kane, who came and ripped the cell door open before executing a Tombstone Piledriver on The Undertaker, which led to Michaels scoring the pinfall.

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4. The Undertaker vs Mankind (Hell in a Cell match), King of the Ring (1998)


Speaking of Hell in a Cell, this was the Hell in a Cell.

Only the second of its kind, the brutality was turned up to 11 from the starting bell as it saw The Undertaker toss Mankind from the top of the cell to the Spanish announcer table and led to commentator Jim Ross saying his legendary line: "As God as my witness, he is broken in half!"

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Mankind came back and climbed back to the top of the cell which led to The Undertaker chokeslamming him through the chain link and onto the ring below as the panel completely gave way. A loose tooth hung beneath Mankind's nose as he bled profusely before continuing the match.

The Undertaker eventually scored the pinfall after a Tombstone Piledriver, but this match certainly elevated (if not shortened, in Mankind's case) the careers of both men.

5. The Undertaker vs Kane, WrestleMania 14


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Following the arrival of Kane in Badd Blood: In Your House in October 1998, The Undertaker continuously refused to engage in a match against his "half-brother," until the Big Red Machine locked up The Deadman in a casket and set it ablaze at the 1998 Royal Rumble, putting this bout in motion.

It was a storyline stroke of genius, with the 7-footers putting up a physical match which also had moments involving their manager Paul Bearer.

The Undertaker did get the victory, but not before hitting three Tombstone Piledrivers on his foe.

After the match, Bearer ordered Kane to attack his brother with a chairshot and a Tombstone Piledriver onto the chair to continue their angle in the coming months.

Their careers, as expected, were intertwined from then on, both as partners as they won the tag team titles thrice as Brothers of Destruction, and as rivals, with them meeting anew at WrestleMania XX six years later.

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6. Bret Hart vs The Undertaker for the WWF World Heavyweight Championship (Special Guest Referee: Shawn Michaels), SummerSlam (1997)


Defending his belt against Hart, one of the best technical wrestlers on the planet, The Undertaker found himself having his hands full. Not only was Shawn Michaels the match's designated official, Paul Bearer and Hart Foundation members Brian Pillman and Owen Hart were also present to distract The Deadman.

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The Excellence of Execution tirelessly cut 'Taker to size as he worked on his legs and even locked a Figure Four on the ring, yet mustered enough strength to go for a chokeslam and a pin. The Hart Foundation, though, distracted HBK which led to The Undertaker choking Michaels before Hart rolled him up.

Hart took a chair, but Michaels intervened, which led to the Canadian spitting on the special guest referee's face. Seething, Michaels went for the Sweet Chin Music as Hart ducked, clocking The Undertaker before he reluctantly counted for the pin.

This match set in motion the aforementioned first Hell in a Cell match and later on, the Montreal Screwjob.

7. Stone Cold Steve Austin vs The Undertaker for the WWF Championship, SummerSlam (1998)


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An absolute classic between two of the best strikers in the company, this was 20-minutes of hard-hitting action which fitted the "Highway to Hell" tagline for the event.

Coming in as the challenger, The Undertaker refused any help from his "brother" Kane as he and Austin tried to beat each other to a pulp with power moves after power moves which meant one small mistake would spell doom.

Unfortunately, it was The Deadman which made that miscue as his OId School attempt was met with a low blow upon his descent, allowing Austin to hit the Stone Cold Stunner for the win.

The Undertaker shockingly gave respect to Austin after the match and handed him the championship before walking off the ring.

8. Kurt Angle vs The Undertaker for the World Heavyweight Championship, No Way Out (2006)


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Like Hart a decade back, Angle was an in-ring technician extraordinaire and showcased his unmatched skills in this main event duel.

The in-ring psychology of this match was off the charts, with the two showing their knowledge of each other's movesets as they repeatedly executed reversal after reversal.

Angle caught The Undertaker with an Angle Slam, but later fell trap to the Hell's Gate triangle choke. The Olympic gold medalist, though, outsmarted The Deadman, countering the submission to a rollup pin to retain his title.

Easily, this match was a show-stealer in a time when WrestleMania 22 was just right around the corner.

9. Edge vs The Undertaker for the vacant World Heavyweight Championship (Tables, Ladders, and Chairs match), One Night Stand (2008)


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Edge stepped up to the plate in the late 2000s as a respectable foil for The Deadman, and them fighting for the title heightened the level of animosity between the two.

And it hit the crescendo at One Night Stand in 2008 as the two fought in the Rated R Superstar's bread and butter: the TLC match.

It was an uphill climb, literally and figuratively, for The Undertaker, as he didn't only need to keep Edge at bay but also deal with his cohorts Curt Hawkins, Zack Ryder, Chavo Guerrero, and Bam Neely.

He almost did, ascending to the top of the ladder, until Edge recovered just in time and pushed the ladder, toppling The Undertaker through four ladders to the outside of the ring.

Due to the prematch stipulation, The Deadman had to leave WWE until SmackDown general manager Vickie Guerrero reinstated him two months later.

10. The Undertaker vs AJ Styles (Boneyard match), WrestleMania 36

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If this was indeed The Undertaker's last, it certainly delivered.

The Undertaker had his apparent curtain call at Night One of WrestleMania 36 as his Boneyard match with Styles definitely knocking the ball out of the park.

Bringing in elements of The Deadman, the American Badass, and the man behind the persona Mark Calaway, The Undertaker had his best match in years, albeit done in a cinematic fashion in an empty backyard lot.

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Styles also brought his A-game, from the club stablemates Karl Anderson and Luke Gallows helping him fight off his legendary foe. Even druids interfered in the match.

But like the mythical being that he is, The Undertaker rose from the dead and pummeled Styles before booting him into the grave and burying him six-feet under.

Take it from the man himself: "If there was ever a perfect ending to a career, that right there is it."

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