The announced clash came out of nowhere but WWE have done an excellent job in the weeks since to sufficiently hype the match and ensure the WWE universe are excited about the two legends colliding once more.
It is difficult to see how the 53 year old Undertaker and the 49 year old Triple H can hope to surpass the quality of some of their previous encounters and better the excellent storyline which proceeded their “End of an Era” clash at Wrestlemania 28 in 2012 which was previously believed to be the final match of their feud.
The hype for the match intensified on the September 3rd episode of Raw, when Triple H’s buddy, Shawn Michaels appeared to give his prediction on the outcome of the bout.
Michaels inevitably predicted that his friend would with the match, which drew the ire of the Undertaker who made a rare appearance to confront him.
Undertaker mocked Michaels for adhering to his retirement vow which he said had less to do with respect and more to do with cowardice at the prospect of facing the “Phenom” once more.
The segment was one of the best on WWE television all year as it perfectly weaved almost a decade of storytelling into the current storyline.
That set up Triple H’s promo on the match on the following week’s episode which although it couldn’t come close to the Michaels-Undertaker segment, was an intense promo nonetheless.
The hype is simmering nicely which means it’s the perfect time to revisit the two legend’s most memorable previous contests with each other.
#5 King of the Ring 2002 (June 23, 2002) - WWE Undisputed Championship
The Undertaker had won the Undisputed Championship from Hulk Hogan the previous month at Judgment Day. Hogan had beaten Triple H for the same title the month before after Undertaker had interfered.
Triple H was out for revenge and the Undisputed Championship once again.
In a back and forth match, Undertaker managed to the hit the Last Ride on “The Game” for a terrific near fall.
At that moment, The Rock interfered taking out Undertaker with a Rock Bottom but the referee was down and couldn’t deliver the count. A low blow to Triple H and a three count later and Undertaker had successfully defended his title.
#4 Monday Night Raw (June 21, 1999) - WWF Championship
Their encounter on Monday Night Raw in June 1999, came amidst The Undertaker’s third reign as WWF Champion.
Triple H was finally starting to gain traction with the fan-base as a legitimate title threat and so the pair clashed in what was their first significant match with each other.
It was a typical Attitude Era brawl wherein the participants fought all over ringside.
It was an entertaining match while it lasted but in truth, this encounter was just a set up for Undertaker’s title defence versus The Rock at King of the Ring six days later.
It was The Rock who caused the finish as he entered the ring and Rock Bottomed Undertaker to cause the DQ finish.
#3 Wrestlemania X-7 (April 1, 2001) - No DQ Match
In their most anticipated bout at that point in time, Undertaker put his undefeated Wrestlemania streak on the line against the Cerebral Assassin.
Unlike their previous bouts, Triple H was heavily favoured to win this encounter due to the astonishing success he had had over the previous 18 months, becoming a 4-time WWF Champion as well as defeating Stone Cold Steve Austin on pay per view weeks earlier at No Way Out.
Triple H had arrived. However, Undertaker had not given up his yard just yet and in a bloody, chaotic brawl that encompassed much of the arena, the pair thrilled the Texas crowd.
As Undertaker lifted Triple H up for a Last Ride, Triple H smashed him in the face with a sledgehammer. Somehow Undertaker kicked out and a further Last Ride earned the victory.
An unforgettable match on one of the best wrestling shows of all time.
#2 Wrestlemania XXVII (April 3, 2011) - No Holds Barred Match
10 years after their classic at Wrestlemania X-7, Triple and The Undertaker clashed once more on the grandest stage.
Their issue? The fact that 12 months earlier Undertaker had retired Triple H’s best friend, Shawn Michaels.
Triple H was gunning for the “Phenom” and for most of the contest held the upper hand. When Triple H executed Undertaker’s Tombstone Piledriver, the match looked to be over.
But Undertaker absorbed the Tombstone and with a brilliant presence of mind locked Triple H into his Hell’s Gate submission finisher. Triple H furiously tried to escape but could not use his sledgehammer to set himself free and was forced to submit.
The fact that Undertaker could not leave the ring under his own power and had to be stretchered out told the story of the match.
Triple H was the winner in all but name but Undertaker’s winning streak was preserved.
#1 Wrestlemania XXVIII (April 1, 2012) - Hell in a Cell Match
In their most epic match yet, Triple H and The Undertaker upped the intensity still further by clashing inside WWE’s most demonic structure, Hell in a Cell.
With Shawn Michaels installed as the special referee, the deck was well and truly stacked against the “Phenom.”
What followed was one of the best-constructed sports entertainment match-ups in company history.
Both men kicked out of each other’s finishers and withstood a huge amount of weapons shots but neither would stay down.
Finally, after kicking out of yet another Pedigree, Undertaker performed another Tombstone that finally put Triple H down for the three count.
With that, the WWE universe thought they had seen the “End of an Era” never expecting the two to clash again.
However, on October 6, 2018, they will and Triple H will be determined to overcome his wretched win/loss record versus Undertaker.
It will be something to behold.
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