The Undertaker vs. Triple H: A match-by-match timeline of their historic rivalry

On Saturday, October 6, two icons will do battle for the last time ever. The Undertaker and Triple H, inarguably one of the greatest rivalries in WWE history, will pin the final chapter of their generational clash at WWE Super Show-Down in Melbourne, Australia.

Despite the sentimental essence of this finale, the lion’s share of this matchup is fueled by the words “unfinished business.” As Attitude Era stalwarts, The Phenom and The King of Kings have battled against each other for the better part of 20 years, leaving an indelible series of five-star matches in their wake. But the thick air of competitive pride shared between them has always overshadowed the decisions of their battles. No matter if it was the “The End of an Era” Hell in a Cell Match at WrestleMania 28 or a No. 1 Contender’s Match for the WWE Championship on Raw, the aftermath has always been spelled out by the age-old phrase: won the battle, but not the war.

As The Undertaker and Triple H face off for the final time to determine, once and for all, who is WWE’s pound-for-pound best, scroll down to trace the deep roots of this epic rivalry featuring all of their one-on-one confrontations.

Singles Match – The Kuwait Cup

Date: May 12, 1996

Winner: Triple H (via Disqualification)

The very first in-ring competition between The Undertaker and Triple H happened overseas in the semifinals of the Kuwait Cup. Though known as Hunter Hearst Helmsley at the time, Triple H was as much The Cerebral Assassin then as he is now. In this hidden gem, The Game did his best to take down The Deadman, who forced his opponent to pull out all the stops. So, he did, too, in the match’s final moments, as Triple H reached for an equalizer that led to his victory – by disqualification, that is.

Watch this match on WWE Network

Intercontinental Championship Match – Shotgun Saturday Night

Date: February 8, 1997

Winner: Triple H (via Disqualification)

One fateful night in February 1997, then-Intercontinental Champion Triple H went one-on-one against The Undertaker inside New York City’s Penn Station. Yes, you read that right. One of the Big Apple’s busiest train stations played host to a then-burgeoning King of Kings and The Deadman, and nothing was the same after. It started with Triple H arriving in a limo and later concluded with the champion sliding down an escalator – by way of a Tombstone Piledriver, of course – all in all going just how anyone could have imagined. This match set the stage for what would come when these two Superstars crossed paths again, in (and out) of the squared circle.

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Singles Match – Raw

Date: April 21, 1997

Winner: No Contest

Scarred, battered, bruised and all, The Undertaker had more on his mind than what would come of his encounter with Triple H during this rare confrontation. But it wasn’t long before The Phenom recognized the downside of having his head out of The Game. Even though Undertaker’s sheer power prevented close calls and vulnerable moments, Triple H’s eye-opening agility and durability kept the WWE Champion from controlling the tempo. Although an interruption by Mankind spoiled the match, it was clear that the conflict between these two Superstars was far from over.

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Singles Match – Friday Night’s Main Event

Date: September 5, 1997

Winner: The Undertaker (via Disqualification)

During a special edition of Friday Night’s Main Event, The Undertaker poured his boiling frustration with Shawn Michaels onto Hunter Hearst Helmsley in a fast-paced battle that saw The Deadman seeking retribution. But just when he came close to doing so, Triple H’s comrades stormed in for the save.

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Singles Match – Raw

Date: September 29, 1997

Winner: The Undertaker (via Disqualification)

For what could have otherwise been announced as a No Holds Barred Match, thanks in part to interferences by Vader, Bret Hart, Rick Rude and Shawn Michaels to name a few, Triple H gave The Undertaker a fight. But none of The Game’s’s offense went unanswered. However, just as The Deadman closed in on delivering a Tombstone Piledriver , Triple H’s outside assistance thwarted those plans.

Watch this match on WWE Network

WWE Championship No Disqualification Match – Raw

Date: June 21, 1999

Winner: The Undertaker (via Disqualification)

With the WWE Championship on the line, Triple H and The Undertaker faced off in a grueling back-and-forth clash that would eventually result in a disqualification, due to interference by The Rock, The Ministry of Darkness and The Big Boss Man.

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No. 1 Contender’s Match – Raw

Date: July 19, 1999

Winner: No Contest

As the sequel to their previous showdown in the Raw ring, Undertaker and Triple H turned the temperature up a few notches in this aggressive No. 1 Contender’s Match for the WWE Championship. Both Superstars traded a slew of near-falls and reversals for most of the bout. In the end, a mudhole-stomping “Stone Cold” Steve Austin and smackdown-laying The Rock would cost them the match, leaving room for wonderment on what would’ve happened had they not interfered in the boiling battle. 

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No Disqualification Match – SmackDown

Date: July 13, 2000

Winner: Triple H

This battle on SmackDown featured chair blasts, ring bell attacks, and a sledgehammer-wielding Kurt Angle. By the end, an ill-fated interference by Angle landed Triple H the victory.

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No Holds Barred Match – WrestleMania X-Seven

Date: April 1, 2001

Winner: The Undertaker

WrestleMania X-Seven will be remembered as the night “Stone Cold” Steve Austin shocked the WWE Universe by aligning with longtime foe Mr. McMahon and Edge pierced Jeff Hardy with a Spear in mid-air, but the best match on the pay-per-view was arguably Undertaker and Triple H’s hellacious melee. Live inside the Astrodome, the phrase “Houston, we have a problem” should’ve been coined that night, because this seismic brawl spilled from the ring to the outside in a matter of seconds. Seriously.

In the first 30 seconds of the bitter rivals hitting the ring, Triple H went smack dab through an announce table by way of a hard right from The Phenom. From there, they traveled through a sea of 67,000-plus attendees, leaving behind laid-out referees and EMTs, to later trade clattering chair blasts, flying elbow drops and a Chokeslam to hell. By the time the heart-stopping action got back inside the ring, the two dominant forces tore the roof off with explosive maneuvers like Triple H thwarting Undertaker’s Last Ride with a sledgehammer attack and The Deadman later exchanging hard haymakers from The Cerebral Assassin with, you guessed it, a Last Ride. While The Demon of Death Valley left the Astrodome victorious, both Superstars were winners, because they undoubtedly pulled out the best from one another.

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No Holds Barred Match – SmackDown

Date: May 17, 2001

Winner: No Contest

“Mess with my family and I will hurt you,” Undertaker announced prior to hitting the SmackDown ring on May 17, 2001. The target of this warning was Triple H, who, together with partner-in-crime “Stone Cold” Steve Austin, tricked The Phenom into thinking his wife had been involved in a car accident. It should almost go without saying, payback was on the brain. Picking up from where they left off a month prior at WrestleMania X-Seven, the two Superstars put on a clinic, nearly mirroring the fury that blew the roof off at the Astrodome. Interferences by Kane and The Texas Rattlesnake would eventually draw the match into a No Contest. Still, the interruptions couldn’t hold a candle to the heat of this battle.

Watch this match on WWE Network

Singles Match – Insurrextion 2002

Date: May 4, 2002

Winner: Triple H

In the words of Good Ol’ J.R., this main event at WWE Insurrextion 2002 was quite the slobberknocker. In this gritty battle of the wills, Undertaker and Triple H took each other to their limits. For every Pedigree attempt, there was a Chokeslam waiting to happen. For every grueling submission hold was a hard-hitting suplex. At one point, the fierce back-and-forth even caused one of the turnbuckles to give out. Both men threw their best at one another in this perfectly paced matchup. More than a traditional match, this battle symbolized a clash of who would be crowned the The Attitude Era’s most dominant competitor. Although it was The Game who secured the three-count over The Phenom, both Superstars put up a fight that left an air of triumph inside the Wembley Arena.

Watch this match on WWE Network

WWE Championship Match – King of the Ring 2002

Date: June 23, 2002

Winner: The Undertaker

The clash at King of the Ring 2002 was far from a mat wrestling classic, but it was unarguably the most contentious bout in the Triple H vs. Undertaker series. The two Superstars were embroiled in a raging rivalry prior to the match, after The Deadman cost The Game his WWE Championship against Hulk Hogan at Backlash. Pushing The Game to the point of no return, it was all-out bedlam when The Last Outlaw entered the ring. No turnbuckle, referee or ringside barrier was safe during the raucous brawl. During one instance, Undertaker dropped  Triple H with Snakes Eyes on an exposed turnbuckle. Ouch. Midway, though, an interference by The Rock would throw both Triple H and Undertaker’s turbulent plans off the rails – that is until the latter pulled off a heinous low blow for the win.

Watch this match on WWE Network

No. 1 Contender’s Match – Raw

Date: August 26, 2002

Winner: Triple H

The Game held nothing back in this No. 1 Contender’s Match for the WWE Championship against   The Undertaker. For a bulk of the competition, Triple H outwrestled his longtime adversary, leaving no room for a repeat of King of the Ring. But while outwrestling him was one thing, outfighting The Phenom was another – and that notion got delivered to Triple H by way of a thunderous Chokeslam in the match’s final minutes. Still, an interruption by Brock Lesnar and a (payback) low blow from The Cerebral Assassin would stop The Deadman from outdoing his longtime opponent.

Watch this match on WWE Network

Singles Match – SmackDown

Date: October 24, 2008

Winner: The Undertaker (via Disqualification)

Goosebumps were raised in this memorable main event, as the reputations of WWE’s two icons were put to test. The contest between Triple H and The Undertaker on this night brought fans on an emotional seesaw, thanks to counters galore and repeated high-risk finishing maneuvers foiled by near-falls. What makes this match shine in the Triple H-Undertaker timeline is how it suddenly went from a physical showdown on paper to a legitimate bout for Attitude Era supremacy. These guys weren’t just putting on a show, they were fighting to prove who is the show. Minus the interruption by Big Show, in here lies the seeds of WrestleMania 27, 28, and, of course, WWE Super Show-Down.

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No Holds Barred Match – WrestleMania 27

Date: April 3, 2011

Winner: The Undertaker

Besides the electric stare-downs, the Chokeslam-turned-Pedigree reversal on the announce table, and, the edge-of-your-seat drama before the Tombstone finale, no moment better symbolized the gravity surrounding this blockbuster contest than what takes place in the opening seconds. Immediately after the sounding of the ring bell, we see a desperate Triple H and a charged-up Undertaker collide, with the former clobbering his target with hard strikes. What makes this a shining highlight is how it effectively evinces the vulnerability of Triple H, as he very plainly wore the high-strung desire on beating the Streak right on his sleeve. On the receiving end of it all, though, Undertaker used every drip of the palpable emotion from his adversary as fuel.

This wasn’t a Retirement Match – The Ultimate Warrior and Randy Savage did compete in one two decades prior at WrestleMania 7, however — but seeing as how these 30 solid minutes of will-he-or-won’t-he drama raised goosebumps, it was almost impossible not to double-check. Sheer strength and cerebral warfare were at play. By the end, the WWE Universe was left with one of the best physical representations of the famous sports-entertainment lexicon: Showcase of the Immortals. Even though The Phenom won the match, it was The Cerebral Assassin who was the last man standing. So, while the battle was done, the war between these two was far from over.

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“End of an Era” Hell in a Cell Match – WrestleMania 28

Date: April 1, 2012  

Winner: The Undertaker

When the wicked fortress landed, entrapping Triple H and Undertaker as they stood centerstage in front of more than 78,000 WWE fans on The Grandest Stage of Them All, other than the emotions billowing in the air, it was crystal-clear that there was to be no other WrestleMania match like this. The minute this massive steel structure surrounded the ring, the intensity that emanated from these two Attitude Era stalwarts indicated that this was about more than just The Streak. It was the culmination of, at that point, an epic 15-year rivalry. The Tombstone on the Penn Station escalator, the slobberknocker at WWE Insurrextion, the low blow at King of the Ring 2002, and the slew of No Contests caused by outside forces that derailed their indominable battles – all of these bottled-up moments flew into a tizzy once the bell rang.

Never mind The Streak and the pinfall, this emotional rollercoaster of a match perfectly encapsulated the well-established timeline that prefaced this moment. A clash of all clashes. A true Goliath versus Goliath matchup. Herein lies the most essential piece to The Undertaker vs. Triple H rivalry. As the sinister structure lifted, so did the dawning of a new era.  

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