Few competitors have meant as much to the world of wrestling as Triple H. A lauded in-ring performer for 30 years, Triple H has also become an influential figure in WWE’s corporate structure since 2010. As crucial as Triple H’s contributions to WWE’s operations have been, his celebrated tenure as an active wrestler is the attribute most people associate with the Game – and for very good reason.

A 14-time world champion, Triple H’s impressive in-ring career speaks for itself. Debuting for WWE in 1995 as the “Connecticut Blueblood,” Hunter Hearst Helmsley, the man who became known as Triple H established himself as a renowned mid-card wrestler in the years that followed. By 1999, Triple H took advantage of his newfound popularity as the leader of D-Generation X to rise to main event status – a position he held for the next two decades, until his retirement in 2022.

Given his lengthy presence in WWE, Triple H has competed against practically every major star in the company. From his Attitude Era feuds against The Rock and “Stone Cold” Steve Austin to his Ruthless Aggression Era bouts against Shawn Michaels and Batista, here are some of the greatest matches Triple H ever appeared in, ranked from best to worst.

Triple H vs. Shawn Michaels (SummersSlam 2002)

After a four-year-long absence from active competition, the Heartbreak Kid Shawn Michaels returned to WWE in 2002. Competing in his first match in four years, Michaels squared off against his former best friend-turned-arch-enemy, Triple H, the two men’s expansive feud kicking off with an Unsanctioned Street Fight at SummerSlam.

Catering to Triple H’s offensive move-set, the Game and HBK’s match made extensive use of foreign weapons, the two trading blows with trash cans, steel chairs, and ladders. A return to form for Michaels, Triple H helped his D.X. stable mate look like an absolute star after his temporary four-year-retirement. Though he met with defeat, Triple H’s feud against Shawn Michaels proved far from over, the two meeting time and time again from 2002 well into 2004.

Triple H vs. Cactus Jack (Royal Rumble 2000)

Winning the WWF Championship for the first time in mid-1999, Triple H became the mainstay heel in WWE for the next two years, joining forces with his on-screen wife Stephanie McMahon to form the villainous McMahon-Helmsley regime. Gaining control of the WWF and using their corrupt rule to dictate matches, Triple H soon found himself opposed by Mick Foley’s boiler room-dwelling persona, Mankind.

Pushing Mankind to the physical and mental breaking point, Triple H received a unique challenge for his world title at Royal Rumble 2000, facing off against Foley’s infamous alter ego, Cactus Jack. In one of the greatest matches of the Attitude Era, Triple H and Foley proceeded to break each other down in a variety of creative manners, bashing each other with barbed wire-strewn two-by-fours and tossing each other into a pool of thumbtacks. A picture-perfect Street Fight, it also helped Triple H win favor among audiences at the time, cementing his place at the top of WWE.

Triple H vs. Shawn Michaels vs. Chris Benoit (WrestleMania 20)

As he defended his World Heavyweight Championship from his recurring foe, Shawn Michaels, Triple H came face to face with a brand-new challenger for his title in the form of 2004 Royal Rumble winner, Chris Benoit. 

One of the best WrestleMania matches in WWE history, Triple H’s Triple Threat match against Michaels and Benoit at WrestleMania 20 has become the stuff of legend. Taking advantage of each man’s working history and chemistry together, the bout made extensive use of dramatic storytelling, alternatively focusing on Benoit’s underdog journey, Michaels’ vindictive mission to beat Triple H, and Triple H’s conniving attempts to retain his title. Though largely erased by Benoit’s personal actions, this bout will forever live on as one of the best in the Ruthless Aggression Era, ending Triple H’s historic world title reign in the best way possible.

Triple H vs. The Undertaker (WrestleMania XXVIII)

Barely walking away from WrestleMania XXVII with his Streak in-tact, The Undertaker issued an open challenge to Triple H for a rematch at WrestleMania XXVIII, hoping to prove he still had what it took to defend his legendary undefeated streak. After some hesitation, Triple H accepted, the two men agreeing to face each other in a historic Cell match with Shawn Michaels acting as special guest referee.

In one of The Undertaker’s best WrestleMania matches, the Dead Man and Triple H put each other through the wringer, delivering punishing maneuvers, sickening chair shots, and abrupt finishers left and right. The  Cell stipulation added a significant degree of excitement to their encounter here, but Michaels’ presence outfitted the bout with a prevalent air of unpredictability. Just as it seemed Triple H might vanquish The Undertaker, though, The Undertaker scored a thunderous Tombstone over his Attitude Era compatriot.

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

Following an almost year-long absence to heal a long-problematic neck injury, “Stone Cold” Steve Austin returned to WWE to find the person responsible for running him over with a car at Survivor Series 1999 (a storyline that helped explain Austin’s absence from television). Learning that Rikishi had performed the hit and run under order from Triple H, Austin began targeting the Game from late 2000 into the new year.

At No Way Out 2001, the Texas Rattlesnake and Triple H went toe to toe in the first ever Three Stages match. With Austin gaining the first pinfall in a standard bout and Triple H winning the second stage under No Holds Barred rules, it all came down to one last showdown in the unforgiving steel cage. With weapons sprawling across the mat, Austin and Triple H pummeled each other across the ring, slamming each other into the chain-link walls and hurling each other from the top rope. A riveting conclusion to a standout feud, it also helped Triple H score another meaningful win over an established Attitude Era legend.

The Two-Man Power Trip vs. Chris Jericho and Chris Benoit (Raw)

After “Stone Cold” Steve Austin’s shocking heel turn at WrestleMania X-Seven, Austin became the preferred ally for Triple H, the duo forming the aptly-named Two Man Power Trip. With Austin holding the WWF Championship and Triple H capturing the Intercontinental title, the pairing managed to quickly secure the WWF Tag Team belts from their mutual rivals in the Brothers of Destruction.

Maintaining control of WWF television for most of May, the Two-Man Power Trip fought an onslaught of worthy contenders for their championship gold, none more so than the odd couple pairing of Chris Benoit and Chris Jericho. In the main event of Raw on May 21, the two teams met in a sensational tag team match – one that ended with Triple H suffering a serious knee injury and Benoit and Jericho walking away the WWF Tag Team Champions.

Triple H vs. The Undertaker (WrestleMania XXVII)

Taking nearly a year off from active wrestling, Triple H returned to WWE in early 2011, challenging The Undertaker to a match at WrestleMania XXVII. Hoping to avenge the loss (and subsequent forced retirement) of his best friend, Shawn Michaels, Triple H also attempted to do what no other man before him had done, ending the Dead Man’s undefeated Streak on the grandest stage of them all.

With a balanced back-and-forth offensive style throughout, The Undertaker and Triple H proceeded to brawl through the ring-side area, smashing into the outside barrier and knocking each other in the head with stiff steel chair shots. With a major chip on his shoulder, a vindictive Triple H came close to beating The Undertaker at his own game, breaking the Streak a historic fashion. But The Undertaker’s resilience ultimately trounced Triple H’s unforgiving brute strength, the Dead Man locking the Cerebral Assassin into a tight Gate submission that ensured the Streak lived on another day.

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

After beating Cactus Jack in their uber-violent Street Fight at the Royal Rumble, Triple H again encountered the Legend, this time within the infamous Cell at No Way Out 2000. The first match of its kind since King of the Ring 1998, the final bout between Cactus Jack and Triple H proved just as unpredictable and exciting as their earlier clash at the Royal Rumble.

Brawling through the cell for most of the match, the two broke out from the steel structure, climbing on top of the cell in a call-back to Foley’s previous Cell match against The Undertaker. While Foley fortunately didn’t replicate his death-defying spot, Triple H tossed Cactus Jack through the top of the cell, sending him crashing into the canvas below. Another extreme match between the Legend and the Game, it continued to illustrate Triple H’s improved in-ring performance, with the Game able to face the best the WWF had to offer at the time.

Triple H vs. Chris Jericho (Fully Loaded 2000)

At the start of 2000, recent WWE arrival, Chris Jericho began accumulating a larger number of supporters among WWE viewers, his newfound popularity guaranteeing him a much-needed push. As Jericho began appearing more often on television, he entered a phenomenal feud against WWE’s most dominant heel at the time: Triple H.

Antagonizing the Game in mid-April, Triple H and Jericho’s feud escalated as the weeks went on, eventually building to a Last Man Standing match between the two at Fully Loaded. As with most non-disqualification matches Triple H has been involved in, the bout turned into a violent brawl, leaving Triple H a pulpy mess at ringside. By the sweat of his scarlet-red brow, though, the Cerebral Assassin pulled one over on Jericho at the literal last second, rising to his feet moments before the referee finished his ten-count.

Triple H vs. Shawn Michaels (Raw)

In the early to mid-2000s, most of Triple H’s bouts against Shawn Michaels were gimmick matches – from their 2002 SummerSlam Street Fight up to their conclusive Cell match at Bad Blood 2004. At the tail end of 2003, however, the estranged D.X. members met in a regular singles match in Michaels’ hometown of San Antonio, headlining the December 29 edition of Raw.

A far more athletic encounter than the Game and HBK’s more violent encounters, Michaels and Triple H managed to conduct a stellar match together, characterized by crisp technical wrestling and rapid counters. Emerging victorious by the scheming machinations of Raw G.M. Eric Bischoff, Triple H’s 2003 bout against Triple H kicked off an exciting new chapter in his feud against Michaels – a chapter that lasted most of 2004.

Triple H vs. The Rock (Judgment Day 2000)

Losing the WWF Championship to The Rock at Backlash 2000, WWE set the stage for a climactic rematch between Triple H and the Great One at the following month’s Judgment Day pay-per-view. Enacting the Iron Man stipulation last seen at WrestleMania XII between Bret Hart and Shawn Michaels, Triple H and The Rock wound up beating each other mercilessly over an entire hour.

A match designed to test the endurance and stamina of each wrestler involved, The Rock and Triple H’s Iron Man bout remains one of the finest hour-long matches in WWE’s history (not to mention the only 60-minute Iron Man match in the Attitude Era). Regularly switching between technical wrestling, fierce brawling, and occasional submission holds, the match demanded a unique performance from each wrestler. As a result, fans witnessed rarely-seen maneuvers from each opponent, whether in the form of The Rock hitting a Pedigree or Triple H performing a Piledriver.

Triple H vs. The Rock (SummerSlam 1998)

In the summer of 1998, Triple H stood opposite burgeoning WWE talent, The Rock. Reigniting their 1997 feud for the I.C. title, both men went on to battle for the Intercontinental Championship throughout mid-1998, the boiling point of their struggle coming at SummerSlam.

Competing in a then-rare Ladder match, the respective leaders' brawl spilled inside and around the Madison Square Garden arena, making tremendous use of the Ladder match format. An intense and physical affair that saw some dramatic interference from Mark Henry and Chyna, it also foreshadowed the theatrical match-ups between the Game and the Great One in 1999 and 2000.

Triple H vs. Shawn Michaels (Bad Blood 2004)

After failing to win back the World Heavyweight Championship from Chris Benoit, Triple H and Shawn Michaels set out to end their multi-year-long feud at Bad Blood 2004, this time within the confines of the Cell. Like nearly all of the previous matches, the match made for a bitter, violent, often gruesome affair, the two men utilizing the Cell structure to maximum effect.

In the longest Cell match to date, Shawn Michaels and Triple spent an unprecedented 47 minutes trading blows, tossing each other face-first into the chainlink walls and bashing each other over the head with steel chairs and ladders. A climactic ending to Triple and Shawn Michaels’ rivalry, it is also one of the greatest Cell bouts thus far.

Triple H vs. Batista (Vengeance 2005)

After a decent but fairly average outing at WrestleMania 21, Triple H and Batista entered a heated rivalry that lasted the rest of 2005's summer season, concluding with a Cell match at Vengeance. The single best match of Batista and Triple H’s extensive feud, it ended up being as grueling a battle as you’d expect from the former Evolution compatriots.

Upping the violence to a solid 11, Triple H and Batista brandished everything from a chain length to a barbed wire-covered steel chair as offensive weapons. A testament to Batista’s rising star power in WWE, Triple H’s valorous efforts to regain his World Heavyweight Championship all came to naught, the Animal putting Triple H away with a deafening Batista Bomb. A solid conclusion to a tremendous feud, it marked the end of an era in terms of Triple H’s three-year-long Reign of Terror.

Triple H vs. The Rock (Backlash 2000)

Cheating his way into a successful title defense at WrestleMania 2000, Triple H’s McMahon-Helmsley regime expanded to include WWE Chairman Vince McMahon. Taking advantage of their new corporate freedom in the company, the Game used his position as McMahon’s hand-picked champ to brutalize his opponents for the next several weeks. Unfortunately for him, a vendetta-driven Rock undermined the McMahon-Helmsley faction around every corner, seeking to avenge his loss at the Game’s hands at the following month’s Backlash pay-per-view.

With the odds stacked in Triple H’s favor, The Rock tried to score a pinfall victory over the Cerebral Assassin, even as Vince and Stephanie wandered around ringside and Shane McMahon acted as the special guest referee. Just as it seemed the overwhelming forces of the McMahons would help Triple H emerge the winner, the decisive arrival of “Stone Cold” Steve Austin evened the playing field, The Rock winning the WWF Championship from Triple H in a heart-rending finish.