Triple H vs. The Undertaker: A Rivalry 23 Years In The Making

It was rumoured for months, confirmed last week, and tonight Triple H addressed it – at the October Super Showdown PPV in Australia, Triple H would face The Undertaker once more, for “the last time ever”. While many joked about how “The End of the Era” match from WrestleMania 28 was supposed to be the last time ever, Triple H clarified that that simply meant the end of the Attitude Era, which both he and Triple H – alongside guest referee Shawn Michaels – were main players in. But he declared the Attitude Era was back for one more match, that will officially be the final pairing of the two multi-time WWE World Champions. Others on Social Media asked if Triple H and The Undertaker is really a rivalry worthy of such a showcase with such billing – but while it may not be Bret vs. Shawn or Rock vs. Austin in terms of historical narrative, the two men have a 23-year rivalry competing against (and with) each other, that lead to two classic WrestleMania match-ups in the last two match ups. Here’s an overview of the 23 year rivalry between “The Game” and “The Deadman”.

Survivor Series 1995

Photo: WWE

The two first made their acquaintance just months after Triple H made his WWF debut in 1995 as the Connecticut blue blood, Hunter Hearst Helmsley. The Undertaker had made his WWF debut five years previous, ironically at Survivor Series in Connecticut. Helmsley was making just his second WWF pay per view appearance, having faced Fatu (Rikishi) the previous month at In Your House 4: Great White North. Undertaker had already been a veteran of four WrestleManias. Undertaker lead a team called The Dark Side, featuring Savio Vega, Fatu and Henry O. Godwinn, against a team lead by Jerry “The King” Lawler called The Royals, that featured King Mabel (Viscera), Triple H, and his dentist Isaac Yankem, DDS (Kane). Helmsley was one of Undertaker’s victims that match, which The Dark Side ultimately won.

Photo: WWE

The Dawn of the Attitude Era

Photo: WWE

They wouldn’t meet in singles action until the WWF’s first trip over to the Middle East as part of the tournament, the Kuwait Cup. The Undertaker defeated Triple H (by disqualification) to advance from the semi finals, but a fire was lit. By the end of 1996, the two briefly fought over Triple H’s new Intercontinental Championship, culiminating in Triple defeating Undertaker to retain his title on an episode of Shotgun Saturday Night in February of 1997. By the spring, The Undertaker was the WWF World Heavyweight Champion, and Triple H got one of his earliest World title opportunities against Taker on RAW that April. By the summer, Triple H had partnered with a new bodyguard, Chyna, and running with his Kliq pal Shawn Michaels in D-Generation X, and Triple H became the Heartbreak Kid’s foot soldier in Michaels’ own World title feud against the Deadman and a surging “Stone Cold” Steve Austin.

The Corporate Ministry

Photo: WWE

The poking at Taker and Austin lead into 1998, even after Triple H took over leadership of DX, when DX (Triple H, X-Pac, Billy Gunn & Road Dogg) would get into a gang war against Taker, Austin and The Legion of Doom (Hawk & Animal). By a year later, the two became team mates in the Corporate Ministry, when DX merged with Vince McMahon and the Undertaker’s Ministry of Darkness. On April 27, 1999, the pair teamed up as a tag team on the very first episode of Smackdown, in a losing effort against “Stone Cold” Steve Austin and The Rock, but they would pair up frequently as the Corporate Ministry storyline continued.

The McMahon-Helmsley Era & The Two Man Power Trip

Photo: WWE

Once the Ministry imploded, The Undertaker returned as the “American Badass”, forming a tag team with his brother Kane, The Brothers of Destruction, and continuing his pursuit of the WWF World Championship. Meanwhile, Triple H had “married” Stephanie McMahon and had formed the precursor to The Authority, the McMahon-Helmsley Faction, which combined a reformed DX with Vince McMahon and Shane McMahon. The Brothers of Destruction, alongside The Rock on some nights, would constantly be challenged by Triple H and his cast of minions. The feud continued through to 2001, when the two would have their first ever pay per view singles match at WrestleMania 17. While Taker would defeat Triple H, that night “Stone Cold” Steve Austin turned heel and joined with Vince McMahon, allying with Triple H in The Two Man Powertrip and taking over the WWE. WWF World Champion Austin and Intercontinental Champion Triple H would sweep the titles by winning the WWF World Tag Team titles by defeating The Brothers of Destruction at Backlash 2001.

Evolution of Evil

Photo: WWE

In the fall of 2002, with Triple H formed a new stable to maintain dominance in the WWE, enlisting his mentor, “Nature Boy” Ric Flair and new faces Randy Orton and Batista into Evolution. With the Undertaker going back to the dark side, he was bound to come head to head against Triple H. The two had two more PPV encounters during this feud, with Triple H defeating Taker at Insurrextion in the London, England, before failing to defeat The Dead Man for the WWE Undisputed World Heavyweight Championship at King of the Ring 2002 later that year. It would be the final encounter of the pair for over six years.

Ruthless Aggression, 2008-2009

Photo: WWE

The two would meet up against for the first time since King of the Ring 2002 on an episode of Smackdown in October of 2008, before briefly teaming up together. The alliance remained into 2009, when Triple H reunited with Shawn Michaels in a new two-man version of DX, as the three had their hands full in feuds together against Legacy (Randy Orton, Cody Rhodes & Ted DiBiase Jr.) and CM Punk’s Straight Edge Society. But as Triple H continued to main event the WWE landscape, the rise of John Cena, Randy Orton and Batista, and the decline in work dates for The Undertaker meant “The Game” rarely saw his former foe.

To End The Streak, The End of An Era

Photo: WWE

In 2011, Triple H looked to even his WrestleMania (0-1) and WWE PPV record (1-2) against The Undertaker by doing what no man had been able to do up until that point – end The Undertaker’s streak at WrestleMania. At WrestleMania 27, the two battled in a hard fought No Holds Barred Match that lasted just shy of 30 minutes. But The Undertaker would prevail, continuing his streak to 19-0.

In 2012, Triple was more determined than ever. He may never even the score with the Undertaker, but he was more obsessed than ever to end the Undertaker’s WrestleMania legacy and “The Streak”. This time, at WrestleMania 28, Triple H faced The Undertaker in a Hell In A Cell Match, with Triple H’s best friend Shawn Michaels as the special guest referee. The odds seemed stacked against Taker, as his age and health was beginning to show. But in another 30 minute war, The Undertaker remained unbeaten, going to 20-0 at the Grandest Stage of Them All. As Triple H mentioned tonight on Raw, Shawn Michaels was rarely seen after that event (having retired from in-ring in 2010), The Undertaker became a rare event, and Triple H himself became more known for his backstage prowess in building NXT than working on the main roster. The last soldiers of the WWF’s Attitude Era had put on the final match of that era indeed.

The Last Time Ever

But now here we are. Six years removed from “The End of An Era” and the two men are going to got at it one more time. Nearly 23 years to the date of their first ever WWF encounter, “The Game” and “The Deadman” are going to put on one last performance. It won’t be The Main Event. It won’t be a Dave Meltzer 8-Star Match. But it will be our final chance to see two men who have travelled the road, fought in the ring, and given their entire lives to the WWE Universe, tell one final chapter, one on one, to their over two decade journey through the annals of WWE history.

Photo: WWE

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