10 Most Memorable Moments From The Undertaker & Triple H's Rivalry

A trip down memory lane before Australia's Super Show-Down...

"Last Time Ever". That would be your tagline for The Undertaker and Triple H's clash at Melbourne's Super Show-Down, coming up the first week of October. Naturally, the "End of an Era" jokes wrote themselves, as matches between the two Attitude Era stalwarts are coasting along the same trajectory as Terry Funk retirements. Surely, WrestleMania 38 will be the "This is It, We Mean It" battle, while the special Argentinian pay-per-view in 2025 will see the two square off in, "Look, There's a Rash of Injuries, And People Like Nostalgia."

Kidding aside, WWE does enjoy their legacy matches, and fans of different generations will have a stake in an Undertaker/Helmsley battle, regardless of their ages. One is a WWE icon of nearly 30 years, looming as both the Batman and the Dirty Harry of the promotion, while the other has been almost as everpresent, finding his way into the day-to-day operations of the company.

Whether or not this in fact their last meeting against each other, it will at least add another memorable moment to a rich and storied shared history that dates back more than two decades. Here are the most notable occurrences in which Undertaker and Triple H crossed paths throughout the years.

10. A Historic Night (1999)


Apparently, being a part of HISTORIC firsts is something that runs in the extended McMahon family. On 25 April 1999, The Undertaker and Triple H would team up in the main event of the maiden episode of SmackDown, which aired as a standalone pilot. Their opponents in said mainer were WWE Champion Stone Cold Steve Austin, and Austin's all-too-recent rival The Rock.

It was earlier that evening that Undertaker's Ministry of Darkness took part in a merger with Shane McMahon's Corporation to form The Corporate Ministry, making Undertaker and Triple H official allies. By the middle of summer, the group would completely blow apart. In the aftermath, The Undertaker would align with Big Show, while Triple H would fulfill his ascent into the World title picture.

9. Tower Of Doom (2001)


The WrestleMania X-Seven slugfest between Undertaker and Triple H is sadly the forgotten sister of the family, paling in terms of historic viability (while taking place at the greatest WrestleMania ever). It's a shame that it doesn't get the mentions the latter two battles do, since it was pretty awesome on its own merits, even if some parts defy logic (i.e. Mike Chioda playing dead for 10 minutes off of an elbow drop).

The most memorable sequence would have to be when the two brawlers ended up fighting through the massive crowd inside the Astrodome, making their way into an elevated production tower. The unique visual of the two duking it out in such a confined space only added to an already-excellent night of action, though the replay for the Chokeslam spot did, unfortunately, expose the soft landing.

8. Fight To The Finish (2009)


If you're of the mind that kayfabe should be accepted as presented, you might wanna skip over this entry here. The 2009 No Way Out pay-per-view saw six men compete inside an Elimination Chamber for the WWE Championship, with two of the individuals just so happening to be our protagonists. Undertaker Tombstoned fellow challenger Jeff Hardy and pinned him, bring the match down to he and The Game.

What followed was a white-hot seven minutes of action, two old dogs scratching and clawing for a chance to hoist the richest prize in the industry once more. In the end, Triple H ended the mini-match with a Pedigree, capturing the gold, therefore having pinned The Undertaker in the middle of the ring. But don't tell WWE this - they might cancel the match.

7. Going Down (1997)


The short-lived Shotgun Saturday Night program is mostly best left forgotten. The show did have its moments, whether it was Marlena's risque distraction of The Sultan, or Terry Funk cursing up a storm. Arguably the coolest moment came when Shotgun emanated from New York City's Penn Station, with IC Champion Hunter Hearst Helmsley defending the gold against Undertaker.

Helmsley would get the win via disqualification, after Undertaker wrestled the belt out of the cheating champion's hands and struck him with it. In the post-match melee, Undertaker chased Helmsley up to Penn Station's second level, flipped him upside down, and delivered a Tombstone Piledriver down one of the escalators. Helmsley sold it by laying unconscious in a seated position, riding the mobile stairs down until some officials received him with the intent to assist.

6. Save The Date (2011)


For weeks, WWE aired these ominous, unsettling videos hyping up something happening on "2.21.11" - a Monday. About halfway into that evening's episode of Monday Night Raw, the final video aired, revealing The Undertaker at the very end. Accompanied by the ached strains of Johnny Cash's "Ain't No Grave", WWE's longtime guardian made his entrance, with few knowing where this all going to lead.

Before Undertaker could utter a sound over the microphone, the solemn air was disrupted by Motorhead, heralding the unexpected arrival of Triple H. Once the two were occupying the same space, they shared silent, hardened glares, with Hunter pacing like a caged animal. When the two came nose to nose, they each made a subtle acknowledgement of the looming WrestleMania sign, which drew a thunderous response. Without saying a word, the two legends sold everybody on their conflict.

5. Fighting Words (2012)


One year after the icy silence between the two men confirmed their WrestleMania XXVII showdown, they used many, many words to etch a rematch into the card for 'Mania 28. This time around, Triple H wasn't the one scratching for a fight, owed to a wave of corporate responsibility overtaking him. Undertaker implored and prodded for another go, but Helmsley wasn't biting the bait.

This continued into the 20 February 2012 episode of Raw, when the two confronted one another, and Triple H maintained his prior stance, adding that ending Undertaker's career would be "bad for business." But Undertaker continued to gnaw at Helmsley's killer spirit, and then drew his ire by not only calling him a coward, but by saying that Shawn Michaels was always better than him. Enraged, Helmsley finally accepted the match, but only if it would be inside Hell in a Cell. And with that, WWE's devil led another soul into temptation.

4. A Narrow Opening (2012)


The End of an Era Hell in a Cell match is a polarizing bout for many. For fans of the match, it was storytelling at its absolute best, a masterful half hour of drama, suspense, and physicality. Others found it to be self-indulgent and, at times, boring. Most will agree that the match had its moments, with one particular hair-raising moment standing out from the rest.

Guest referee Shawn Michaels played an important role in the Cell, insinuating himself into the drama and earning a choke-out via Hell's Gate. Michaels recovered some time later while Undertaker was lifting Triple H for a Tombstone. Out of anger, Michaels Superkicked 'Taker, which led to a Triple H Pedigree, and a very close two count off of the double-finish. The times before the Streak's demise when it seemed as though Taker was losing are few, but this was certainly a heart-stopper that belongs on that list.

3. "He's Here" (2000)


Biker 'Taker was birthed in the closing moments of a 60-minute Iron Man match at the 2000 Judgment Day, pitting Triple H against WWE Champion The Rock. Amidst all the chaos with the interfering McMahon-Helmsley regime, the creepy nursery rhyme with the three little girls played on the Titantron, signalling something drastic at hand. The sound of a revving motorcycle beneath the words "now back from the dead" was his cue.

Undertaker, following an eight-month injury layoff, stormed the ring with furious vengeance, wiping out everybody in his path, including DX and the McMahons. Triple H suffered a Chokeslam and a Tombstone for his troubles, but those deadly moves had the unintended consequence of The Game regaining the WWE Championship via disqualification. As for Undertaker, his run as WWE's uneasy rider would last three-and-a-half years.

2. Within An Inch Of Oblivion (2011)


Prior to WrestleMania XXVII, what was the last time the Undertaker's Streak felt like it was in jeopardy? Maybe in the closing stages of the Shawn Michaels' matches, but even then, not really. Going back to Legend Killer Randy Orton's RKO Outta Nowhere at 21, you may have felt WWE was about to pass the torch there. Otherwise, we all grew to take the Streak for granted.

That's why when Triple H beat Undertaker down into a fragmented shell at 'Mania 27, it came off as so shocking. The chair to the head, the Tombstone on the man himself, etc, all felt like a fast track to the end, especially as Undertaker sold as though he were in his death throes. But he would manage to stave off mortality for another year when he snared Triple H into the Hell's Gate, narrowly wresting a submission from his foe. It may have been the most dramatic finishing sequence of any of Taker's Mania bouts.

1. An Era Ends? (2012)


The end of The End of an Era flipped the script on the previous year, with Triple H now in the role of the stumbling dead. Undertaker broke Helmsley's body, mind, and spirit, going so far as to tell referee Michaels to just put his friend out of his misery. Helmsley's last gasp with the sledgehammer only led to him eating a few more bullets, before Undertaker shovelled the last piles of dirt himself.

The enduring image from the post-match saw Undertaker and Michaels aid a pained, lifeless Helmsley up the long rampway, before turning to face the 70,000+, stoically basking in a massive standing ovation. Some took End of an Era to be literal, that it was the swan song for all three men. But in wrestling, nobody ever truly goes away. And a phrase like Last Time Ever, well...

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Justin Henry

Written by Justin Henry

In addition to writing lists and commentaries for Cultaholic, Justin is also a features writer and interviewer for Fighting Spirit Magazine, and is co-author of the WWE-related book Titan Screwed: Lost Smiles, Stunners, and Screwjobs.