5 Best Undertaker vs Triple H matches

Rolling a few years back.
A Nostalgia Trip back to the Golden Days.

In what is being billed as a Last Time Ever Match, Undertaker will once again lock horns inside the WWE ring with his longtime rival and WWE COO Triple H when WWE travel Down Under for their MCG Special named Super Showdown.

While it clearly doesn't make any sense to have these two face each other off again, six years after their last encounter, WWE is supposedly going all out by promoting this as the marquee match for the show at Melbourne.

Two of the most prominent names in the history of professional wrestling, The Undertaker and Triple H are no strangers to each other, having faced each other and beside each other, in some of the all-time classic matches for a better part of the last two decades.

Even though both of them are way past their prime, the build to this match has taken all wrestling fans to a nostalgia trip to the golden days.

Whether or not this match will deliver, only time will tell. Till then, here is a nostalgic recall to the five best one-on-one matches between The Phenom and The Game.


#5 Singles Match (Insurrextion 2002)

This was one of those rare instances where The Undertaker was a hated villain and Triple H was a beloved fan favourite. With Taker in the midst of his Big Evil persona in early 2002, he was easily the biggest heel in the entire WWE.

After costing Triple H his Undisputed Title by interfering in his match against Hulk Hogan at Backlash 2002, he began a feud with The Game that had the two fight each other in two pay per view clashes.

While their second clash at King of the Ring 2002 for Undertaker's Undisputed Title was a boring and disappointing affair, their first clash, which happened merely a month before the second, is an underrated classic.

As the main event of the UK-exclusive Insurrextion event, the two fought a hard-hitting contest in front of a vocal London crowd.

There was not a single dull moment in this 13-minute clash. Both the in-ring veterans had to improvise the match after the top rope was loosened up after an Irish Whip to the Big Evil.

The closing moments of the match were full of drama, with both superstars either reversing or kicking out of their opponents finishers. However, it was Triple H who was the last man standing as he successfully countered a Snake Eye into a pedigree for a memorable win.

#4 Singles Match (WWE Smackdown 2008)

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WWE doesn't usually give out pay per view caliber matches on free television, but on this occasion, not only did they give away a high profile match on television taping, they did so with two of the biggest superstars in the history of the organisation.

In late 2008, just a few days shy of Cyber Sunday, WWE brought together Taker and the then WWE Champion Triple H together for a match on a taped episode of Smackdown.

Unlike all the other matches on this list, there was no backstory and real animosity between these two gladiators.

Both were scheduled for high profile matches, against Vladmir Kozlov and Big Show, at Cyber Sunday.

Yet, in their first match against each other in over six years, the two clicked so brilliantly that it produced one of the best matches in the history of Smackdown.

In a match that lasted just a little under 12 minutes, the two showed once again why they were called legends and wrestled a match pretty much similar to the match they had at Insurrextion six year earlier.

With counters and reversals, the two enthralled the fans until The Big Show interfered, caused a disqualification and knocked both HHH and Taker out with chairs. Who knows, had Big Show not interfered, maybe the two could have wrestled the best Smackdown match ever.

#3 No Holds Barred Match (WrestleMania XXVII)

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Well, this is where things take an interesting turn. I know I might get some flanking for choosing the next match ahead of this one, but I have my own reason for placing it below the next one.

This was the second of the three WrestleMania matches that these two stalwarts had over a period of 11 years and was one of the most jaw-dropping matches of the year, maybe even this decade.

Even then, the match ranks as the weakest among the prestigious trilogy of matches that they shared.

With a lot of the build-up revolving around Triple H's obsession with revenging Shawn Michaels defeat from a year ago, the animosity and buzz for this match for way, way more than any other match on a loaded WrestleMania XXVII card. The added stipulation of No Holds Barred ensured that the action won't just be reduced to the inside of ring.

As the sole bright spot on an overall disappointing Mania, this match saved the show from ending up as the worst edition in the history.

With a ton of emotions and drama, the two wrestled a near half-hour classic that had a whole bunch of chair shots, finisher reversals, stolen finishers and a magnificent announcer table spot. You'd be lying if you didn't have goosebumps when Taker kicked out of Triple H's Tombstone Piledriver.

Taker's victory, and the aftermath of the match, where he collapsed at ringside, laid the foundation of a sequel a year later.

#2 Singles Match (WrestleMania X-Seven)

This is a match that often gets lost in the shuffle of some underrated classics. While it didn't have the emotion and drama that the match at WrestleMania XXVII had a decade later, the quality of in-ring work and the backstory involved during the build of this match forced me to put this match from 2001 at the penultimate spot on this list.

Plus, it took place on the best show in the history, so that also played a big part in deciding these two spots.

Unlike the previous two entries, there was a proper heel-face dynamics in this rivalry. Triple H was in the midst of his McMahon-Helmsley Faction period, and, having defeated Stone Cold at the previous show, was the biggest heel on the entire roster.

With Taker promising to make him famous, the two consistently targeted each other, with HHH getting Taker arrested and Taker asking Kane to hold Stephanie McMahon on the balcony for this match at Mania.

In front of a record-breaking crowd in Houston, the two started battering each other even before the bell rang, and continued to assault each other for several minutes.

The match is also famous for that lengthy referee bump, when, with the referee knocked out cold, Taker and HHH fought through the crowd that ended with Taker chokeslamming HHH off a production unit.

The final few minutes saw a handful of finishers, close calls and even blood loss before Taker retaliated with a Last Ride to pin HHH and win this 18 minutes gem.

#1 Hell in a Cell Match (WrestleMania XXVIII)

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Was there ever any doubt? If there was, then you need to stop calling yourself a true wrestling fan.

This was the 'END OF AN ERA' match, for God's sake. Not only did it have Undertaker and Triple H fight each other for a record third time, and second consecutive time, at WrestleMania, it had a guest referee and a Hell in a Cell stipulation. What else do you need to produce an all-time classic?

Picking up right where they left at WrestleMania XXVII, Undertaker continuously challenged HHH to a rematch in order to remove the image from their match a year ago.

HHH initially refused, but after Taker taunted him for being a coward and for being inferior to Shawn Michaels, HHH agreed to a Hell in a Cell match.

After being berated by both participants, Michaels was included into the match as a special guest referee.

On a night where The Rock and John Cena wrestled a dream cross-generational match, it was Triple H and Undertaker that stole all the limelight.

The brutality and ferocity shown by the two legends in this match was something that had not been seen in the WWE for a long time. Even Shawn Michaels made his presence felt when he superkicked Taker into a pedigree for the closest call in the history of WWE.

Plenty of chair shots, sledgehammers and finishers later, Undertaker won the 31 minutes all-time classic to bring an end to a classic rivalry and a dream era.

The image of Michaels, Taker and HHH hugging on the stage post-match remains one of the most iconic images in the history of professional wrestling.

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