Smark Out Moment

On April 30th, 1995, the then-WWF audience was introduced to a pompous, self-centered American Blueblood by the name of Hunter Hearst Helmsley. 25 years, 14 world championships and countless matches later, Triple H is unquestionably one of the most enduring and decorated superstars in WWE history.


And The Game's legacy now extends far beyond his time between the ropes. The son-in-law of Vince McMahon and an Executive Vice President at the summit of the company, Triple H is the forefather of NXT and one of the heirs apparent when McMahon finally relinquishes his iron throne.

But first and foremost, Triple H is a wrestler, and his 25 years in the company has contributed to legendary clashes that are fondly remembered to this day. And here, I want to celebrate The King of Kings' incredible milestone by counting down what I believe to be the greatest matches of his storied WWE career.

25. Triple H vs Kurt Angle vs The Rock vs Steve Austin vs The Undertaker vs Rikishi (Armageddon 2000)

Kicking off with one of the wildest matches of the entire Attitude Era, Triple H joined 5 other top tier superstars inside (and indeed outside) Hell in a Cell. With brawling around the arena, weapons aplenty, high-risk bumps, outside interference and a hot crowd, it is really a quintessential match for that period in WWE's history. And, it goes without saying, this won't be the last Hell in a Cell match featured on this countdown…

24. Triple H vs Sting (WrestleMania 31)

While Triple H was not the first opponent many had in mind for Sting's first-ever match in WWE, their clash featured a fun homage to the Attitude Era, including interference by DX and the nWo. In the end, The Game and his trusty sledgehammer secured the unexpected victory.

23. Triple H vs Randy Orton (No Mercy 2007)

Despite a rivalry spanning many years, Triple H vs Randy Orton is not a feud littered with classic matches. However, all the way back in 2007, in their second match of the night (and Triple H's third overall), they delivered on all cylinders in a brutal Last Man Standing Match, with The Game dropping his newly won WWE Championship to The Viper.

22. Triple H vs Cactus Jack (Raw, September 22, 1997)

The oldest match on this countdown, this fun hardcore brawl is most fondly remembered for the "3 Faces of Foley" skit that preceded it, introducing Cactus Jack to the WWF audience. For Hunter Hearst Helmsley, this was a truly breakout match, and an action-packed prelude to what would arguably be the most pivotal rivalry of his entire career.

21. Triple H vs The Undertaker (WrestleMania X-Seven)

Two of the most distinguished veterans in WWE today met for the first of three WrestleMania bouts back in 2001, and it unquestionably proved The Undertaker's finest match of his Streak up to that point. With plenty of fist-fighting around ringside and a stellar finishing sequence, this battle still only scratched the surface of what Triple H and The Undertaker could achieve on the Grandest Stage of Them All.

20. Triple H vs Dean Ambrose (Roadblock 2016)

Triple H's final run as WWE Champion will always be synonymous with that dreadfully disappointing WrestleMania 32 main event against Roman Reigns. Yet, this gem from a few weeks prior demonstrated that Dean Ambrose had all the makings of a bonafide main eventer, and that, with the right opponent, Triple H could still have a gripping (albeit long) match with this generation's superstars.

19. Evolution vs The Shield (Extreme Rules 2014)

Evolution's reformation in 2014 put the iconic trio on a collision course with WWE's hottest faction at the time - The Shield. Having recently turned babyface, this full-blooded Six-Man Tag saw the young lions overcome the veterans, and going a long way to establishing Roman Reigns, Seth Rollins and Dean Ambrose as the future standard-bearers of the company.

18. Triple H & Stephanie McMahon vs Kurt Angle & Ronda Rousey (WrestleMania 34)

While not technically as proficient as many of the other matches on this countdown, this Mixed Tag was still pro wrestling at its finest. Ronda Rousey shone in her in-ring debut, helped by Triple H dutifully selling for the future Raw Women's Champion. Add a hard-working Kurt Angle and Stephanie McMahon getting her comeuppance, this match was the standout highlight of WrestleMania 34.

17. Triple H vs The Rock (SummerSlam 1998)

Before they would go onto dominate the main event scene in the early 2000s, Triple H and The Rock gave a promising glimpse into their future rivalry in this Ladder Match for the Intercontinental Championship. Although the gimmick was neither man's forte, they pushed each other to their limit in a show-stealing performance, with The Game capturing the gold for the second time.

16. Triple H vs Shawn Michaels (Bad Blood 2004)

The feud that defined the years 2002 to 2004 was the implosion of the founding fathers of DX, Triple H and Shawn Michaels. And the culmination of this was an epic (if slightly over-indulgent) 47-minute Hell in a Cell battle. Incorporating ladders, tables and tons of bloodshed, it was Triple H that stood tall at the conclusion, finishing off Michaels with back-to-back Pedigrees.

15. Triple H vs The Undertaker (WrestleMania 27)

For their second WrestleMania clash, Triple H and The Undertaker took things up a notch. Adding a No Disqualification stipulation and playing off of The Phenom's retirement of Shawn Michaels the year prior, the match saw The King of Kings destroy The Deadman for much of the match, including nailing his own Tombstone Piledriver, before succumbing to the Hell's Gate.

14. Triple H vs Batista (Vengeance 2005)

Triple H is accused (often justifiably) of burying others to protect his position on top of the card. But one man he didn't keep from ascending to the summit was Batista. After already falling twice to The Animal at WrestleMania and Backlash, the two went to war one last time inside Hell in a Cell. Battling through barbed-wire chairs, sledgehammers and steel steps, a devastating Batista Bomb saw The Game go down once and for all.

13. Triple H vs Chris Jericho (Fully Loaded 2000)

An often-overlooked classic of an underrated rivalry, Triple H and Chris Jericho clashed in the very first Last Man Standing match in WWE history. The intensity and brutality of this match went a long way in establishing Jericho as a future World Champion, as well as launching his storied rivalry with Stephanie McMahon. But, as is often the case in this equation, it was Triple H who beat the count to claim this history-making victory.

12. Triple H vs The Rock (Judgement Day 2000)

The feud that lit up the year 2000, Triple H and The Rock clashed for the WWF Championship in only the second 60-minute Iron Man match in company history. Unlike its predecessor, this match was packed with pinfalls, disqualifications and interference, as both pushed their bodies to the limits. Add in Shawn Michaels as a guest referee and the return of The Undertaker after a lengthy hiatus, this was a highly engaging main event, with Triple H regaining the title in a 6-5 scoreline.

11. Triple H vs Cactus Jack (No Way Out 2000)

While the stipulation didn't stick, thanks to this match Triple H has always been able to proclaim that he retired Mick Foley. Foley went all out in what he envisioned was his final match, including a terrifying bump through the roof of the Hell in a Cell through the ring. However, Triple H cemented his status as WWF Champion by pinning the Hardcore Legend and closing the book on his incredible career (for a couple of weeks at least).

10. Triple H vs Chris Benoit vs Shawn Michaels (Backlash 2004)

While it didn't quite have the magic of their WrestleMania XX clash, the sequel to this historic Triple Threat Match didn't disappoint in the slightest. Powered by a ravenous hometown crowd behind Chris Benoit, Shawn Michaels being berated by "You screwed Bret" chants and the same stellar dynamic between all three performers, Benoit reinforced his reign as World Heavyweight Champion by forcing Michaels to tap out.

9. Triple H vs Daniel Bryan (WrestleMania XXX)

In a match that many consider the greatest opening contest in WrestleMania history, Triple H looked to kill off Daniel Bryan's dreams of becoming WWE Champion at WrestleMania XXX. Going over 25 minutes packed with crisp, emotion-fuelled wrestling, Bryan connected with a running knee to defeat The Game, giving him the momentum he needed to capture the gold in the night's main event.

8. Triple H vs The Rock (Backlash 2000)

Although this match happened a month later than it should have, Triple H and The Rock was a main event with every Attitude Era trope imaginable. Weapon shots. Interference. Special guest referees. McMahons everywhere. A raucous crowd. Stone Cold saving the day. And in the end, The Great One overcame all odds to end Triple H's reign as WWF Champion.

7. Triple H vs The Undertaker (WrestleMania 28)

The match billed as 'The End of an Era' might have proven inaccurate, but Triple H and The Undertaker delivered a clash worthy of that moniker. In their third and final WrestleMania clash, held inside Hell in a Cell and with Shawn Michaels as the referee, The Game came closer than anyone at that point to ending The Deadman's Streak. But, once again, he tasted defeat on The Grandest Stage of Them All, before all three men left arm-in-arm.

6. Triple H vs Shawn Michaels vs Chris Jericho vs Kane vs Booker T vs RVD (Survivor Series 2002)

Few gimmick matches have endured the test of time like the Elimination Chamber, and a big contributor to this is the quality of its first outing. Triple H was the glue of this 6-way war, being there from start to finish despite a throat injury caused early on by RVD. After over half an hour, the crowded field came down to Triple H and Shawn Michaels, with HBK capturing the World Heavyweight Championship in front of a wild Madison Square Garden crowd.

5. Triple H vs Shawn Michaels (SummerSlam 2002)

The brotherhood that once united Triple H and Shawn Michaels in 2002 transitioned into one of the most intense rivalries of the past 20 years. In HBK's first match back in WWE after a back injury in 1998 seemingly ended his career, this Street Fight removed any doubts that Michaels could still go, with the Cerebral Assassin at his dastardly best. And although Michaels won the match, The Game (and his sledgehammer) was the only one able to walk out of the ring.

4. Triple H & Steve Austin vs Chris Jericho & Chris Benoit (Raw, May 21, 2001)

For many people, this is the greatest match in Raw's storied history. With Triple H & Stone Cold Steve Austin running roughshod over WWE as The Two Man Power Trip, the crowd were desperately behind the underdog pairing of Chris Jericho & Chris Benoit. An excellent match followed, which included the infamous moment of Triple H tearing his quadriceps for the first time. However, he toughed it out until the very end, as Jericho & Benoit captured the World Tag Team Championships.

3. Triple H vs Steve Austin (No Way Out 2001)

A few months prior to teaming up, Triple H and Steve Austin were at each other's throats after The Game was revealed as the mastermind behind Austin being run over at Survivor Series 1999. This 3 Stages of Hell was a titanic battle, with Austin winning the opening Singles Match and Triple H getting the better of a Street Fight. Finally, inside a Steel Cage with weapons strewn all over the ring, The Game was victorious by the skin of his teeth, ending their heated rivalry for good.

2. Triple H vs Chris Benoit vs Shawn Michaels (WrestleMania XX)

WrestleMania XX was the culmination of an 18-year journey for Chris Benoit, one that has been marred by the circumstances surrounding the end of his life. But, the match that led to this moment remains one of the greatest WrestleMania main events in history. In front of a rabid MSG audience, Triple H, Shawn Michaels and Benoit delivered an absolute classic, ending with The Game forced to tap out to the Crossface.

1. Triple H vs Cactus Jack (Royal Rumble 2000)

The match that 'made' Triple H in the eyes of many also took place at MSG, and it was the ideal stage for such a violent, physical and intense match. With the WWF Championship at stake, Cactus Jack forced The Game to dig deeper than he ever had before to secure a victory, which Triple H was eventually able to accomplish after a Pedigree into hundreds of thumbtacks.

It's impossible to do all of these matches justice with just words, so I'd urge anyone to check these out for yourself if you haven't seen them before (or if you're just looking for a fun way to pass the time in quarantine). And, if it isn't clear already, this ranking is just my personal opinion - feel free to include any more of Triple H's top matches in the comments below!