The rivalry between Triple H and The Undertaker played a massive role in each of their respective careers. Undertaker and Triple H worked together for almost three decades in WWE with various chapters of their rivalry. WWE would place them in feuds when it made sense for each character or when they wanted a big attraction.
Fans typically loved seeing the two work together, especially when they became legends towards the latter stages of their careers. Three WrestleMania matches and many more memorable moments will always link them together. The following aspects of the Triple H vs Undertaker rivalry provide a deeper look at forgotten times.
10 Kane Threatening Stephanie Confirmed Their WM 17 Match
WWE was on fire heading into WrestleMania 17 and showed it with an all-time great card. Steve Austin vs The Rock was slated into the main event for the biggest possible attraction, but WWE also wanted a massive semi-main event.
The Undertaker and Triple H had their first WrestleMania match here with a unique build. Commissioner William Regal was against booking the match until Kane abducted Stephanie McMahon and threatened to throw her off a high platform. Triple H was forced into the match with his wife’s safety threatened by Undertaker’s brother.
9 Triple H Pinned Undertaker To Win Title In Elimination Chamber
WWE had one of the most shocking Elimination Chamber matches at No Way Out 2009 when WWE Champion Edge was eliminated first. The moment ensured a new champion with the five other challengers remaining.
Triple H and The Undertaker may have had the best final exchange, being the two last legends left in the match. The ending saw Triple H beating Undertaker with a Pedigree to once again hold the WWE Championship heading into WrestleMania 25.
8 Had A Match in Penn Station
The unique concept of Shotgun Saturday Night saw the shows taking place in unusual locations like bars and nightclubs. Triple H and The Undertaker might have wrestled in the oddest setting when their match took place at Penn Station.
The New York train station was massive and held the ring for a match between the future legends. Undertaker ended it in memorable fashion by hitting a tombstone on Triple H at the top of an escalator as his body went down with it to end the show.
7 Undertaker Accidentally Helped Triple H Win WWE Championship As Enemy
The debut of the American Badass persona of The Undertaker came at Judgment Day 2000 during an Iron Man match between Triple H and The Rock. Undertaker initially arrived to even the odds when various members of the McMahon-Helmsley Regime interfered.
However, the special guest referee Shawn Michaels noticed Undertaker hitting a chokeslam on Triple H right as the time limit was expiring. A disqualification victory for Triple H broke the tie to win him the WWE Championship back from Rock.
6 Forgotten 2002 Title Feud
The spring of 2002 featured the WWE Championship involved in a few awful PPV matches. Hulk Hogan won the title from Triple H when he turned face to play into the momentum, but The Undertaker won it from Hogan a month later.
WWE set up Triple H’s big title rematch for King of the Ring 2002 challenging Undertaker. The match was only remembered for The Rock’s return and the entire feud felt off. This was the least memorable chapter of the rivalry between the two legends.
5 WM 28 Was Supposed To Be Final Match
WWE intelligently marketed the WrestleMania 28 match between Triple H and The Undertaker as the end of an era. Shawn Michaels being added as a guest referee along with the Hell in a Cell stipulation made it feel like a special time for fans.
This ended up being one of the all-time great WrestleMania matches with Undertaker continuing the undefeated streak. WWE eventually went back on this by having them wrestle years later, but the finality was a huge part of the story at the time.
4 Both Regretted Final Tag Match
A huge show in Australia saw The Undertaker and Triple H having their final singles match, but it was done to set up a bigger tag match. Shawn Michaels costing Undertaker the match led to Michaels coming out of retirement for one of the cash-grab Saudi Arabia shows.
D-Generation X reformed with Triple H and Michaels going against Undertaker and Kane as the Brothers of Destruction. All four legends seemingly sold their soul for one night with an all-time bad performance. Backstage footage after the match aired on Undertaker’s documentary series, showing them all acknowledging how bad it truly was.
3 Undertaker Refused To Wrestle Triple H As Part Of Storyline
The most forgotten noteworthy storyline for The Undertaker featured him breaking the fourth wall and referencing his dead man gimmick not being real in 1999. Undertaker broke character a few times when having worked shoot promos with Vince McMahon.
A demand from Vince for Undertaker to face Triple H in a casket match saw the legend walking out and giving up his WWE Championship match. The angle was done to have Undertaker rehab an injury, but WWE never picked it back up when he returned in 2000.
2 Used Sting Rumors To Create Match
The shocking returns of both The Undertaker and Triple H ahead of WrestleMania 27 featured a lot of interesting elements to the build. WWE running cryptic promos for months created huge speculation of Sting making his WWE debut to finally challenge Undertaker.
The company realized that just Undertaker returning would be too predictable and fans may be disappointed at the lack of Sting since he ended up re-signing with TNA. Triple H returned that same night as Undertaker after a long break to set up their big match.
1 Continued Feud In Tag Action After WM 17
The Undertaker defeating Triple H at WrestleMania 17 is viewed as the end of that chapter of their feud since they didn’t have another singles match for another year. However, it continued in another form when the right timing for another major star’s character change played out.
Steve Austin turning heel to align with Vince McMahon led to him forming the infamous Two-Man Power Trip team with Triple H. The first storyline for Austin and Triple H saw them beating Undertaker and Kane to win the WWE Tag Team Championship.