For nearly three decades, Triple H was an in-ring performer with WWE and his career speaks for itself. He's a 14-time WWE World Champion, a five-time Intercontinental Champion, a two-time European Champion, and he's won multiple WWE World Tag Team Championships. Triple H has also headlined WrestleMania with success and heartbreaking losses on several occasions.
The Game has been tough to beat over the years, especially in one-on-one matches on WWE premium live events. However, some wrestlers have managed to get the better of the Cerebral Assassin which is no mean feat.
23 The Ultimate Warrior
Triple H's maiden WrestleMania outing at WrestleMania 12 did not go according to plan. He faced off against former WWE Champion The Ultimate Warrior who returned to WWE for the first time in four years.
It was a humiliating night for Triple H as Warrior tore through him with ease. It's not a match that Triple H will revisit soon, with Warrior besting Triple H in under two minutes.
22 Marc Mero
In Your House 8: Beware of Dog is best remembered for the bad weather which affected the show. However, Triple H went toe-to-toe with Marc Mero and he lost to him in a match that almost spanned 20 minutes.
They locked horns in the final premium live event with Triple H's Intercontinental Championship on the line. Mero registered another win over Triple H but didn't take home the Intercontinental Title as he won by count-out.
21 Steve Austin
The first one-on-one match on a PLE in the storied rivalry between Triple H and Steve Austin took place at In Your House: Buried Alive. This was a fantastic match between the pair in the curtain-raiser.
Both Triple H and Austin were on the way up in 1996, and Austin got the win over Triple H. Surprisingly, it's Austin's only win over Triple H in a singles match on a WWE premium live event.
20 Mankind
Triple H and Mankind's feud was one of the most physical in WWE history. Triple H was looking to continue his success over Mankind when they squared off in a steel cage match at SummerSlam 1997.
As expected, they knocked it out of the park in a brilliant contest. The match went back and forth with both gaining the upper but it was Mrs. Foley's Baby Boy who gained the bragging rights.
19 The Rock
The matches between Triple H and The Rock were always entertaining affairs. Rock retained the Intercontinental Championship against Triple H at In Your House: Final Four to continue his maiden run as Intercontinental Champion.
Rock beat Triple H albeit by disqualification at Over the Edge 1999. Moreover, his most significant win over Triple H was at Backlash 2000 when he defeated him to become a four-time WWE Champion.
18 Kane
Triple H represented DX and Kane represented the Corporation in their one-on-one match at WrestleMania 15. Chyna was a member of the Corporation but she rejoined DX with Kane defeating Triple H by disqualification.
Two years later, Triple H and Kane clashed in a chain match for the Intercontinental Championship at Judgment Day 2001. It was an underrated bout, and the Big Red Machine became a Grand Slam Champion when he took the Intercontinental Title away from the Game.
17 Kurt Angle
The feud between Triple H and Kurt Angle was exceptional, and their matches together were superb. At the 2001 Royal Rumble, Angle overcame Triple H to retain the WWE Championship with a helping hand from Steve Austin.
The stakes were high in their match at No Way Out 2002 as Triple H's WWE Championship opportunity at WrestleMania 18 was on the line. However, Triple H's ex-wife Stephanie McMahon was the special guest referee, and Angle bested Triple H once more.
16 Hulk Hogan
Triple H and Hulk Hogan's WWE Championship match at Backlash 2002 was incredibly boring. The Hulkster was far from his best, but he was awarded this title match after he had a good outing against The Rock at WrestleMania 18.
Hogan had no right to win this match, but he did as The Undertaker interfered and he cost Triple H the WWE Championship with Hogan kickstarting his sixth and final WWE Championship reign.
15 Shawn Michaels
Shawn Michaels made his in-ring return to action for the first time in four years, and he collided with Triple H in an Unsanctioned match at SummerSlam 2002.
HBK did not miss a beat in this match, and it was a fantastic wrestling match between the two former best friends. The Game was going for the Pedigree but Michaels reversed it with a jackknife cover to earn the win.
14 Scott Steiner
Fans were subjected to a dreadful World Heavyweight Championship match between Triple H and Scott Steiner at the 2003 Royal Rumble. Their chemistry was non-existent, and it was one of the worst matches in the Game's career.
Big Poppa Pump was in a commanding position to get his hands on the Big Gold Belt. Ultimately, Triple H was resourceful as he got himself intentionally disqualified with Steiner victorious but Triple H kept his title intact.
13 Kevin Nash
Triple H was dominant in 2003 with his reign of terror taking a stranglehold of proceedings on Raw. The Game defended the World Heavyweight Championship against Kevin Nash at Judgment Day.
Their series of matches were poor, and this was the worst of the lot. Big Daddy Cool was a threat to Triple H's World Heavyweight Championship but the Cerebral Assassin got disqualified with Nash taking out his frustrations and he connected with the Jackknife on Triple H through the broadcast table.
12 Goldberg
SummerSlam 2003 saw Triple H overcome Goldberg in an Elimination Chamber match to retain the World Heavyweight Championship. However, the stakes were high in their one-on-one bout at Unforgiven 2003 with Goldberg forced to leave WWE if he failed to win the title, but Triple H could lose it by DQ or count-out.
The Game's 280-day run as World Heavyweight Championship run was curtailed by Goldberg. Months later, they had a rematch at Survivor Series with Goldberg once again coming out on top in a successful title defense.
11 Batista
Batista departed Evolution at the start of 2005, and he set his eyes on Triple H's World Heavyweight Championship. At WrestleMania 21, the Animal ended the Game's 10th World Championship run.
They competed in a couple of rematches at Backlash with Batista overcoming Triple H again. Their third and final meeting in their series of matches saw Batista become the first man to beat Triple H in one-on-one Hell in a Cell match at Vengeance.
10 Ric Flair
Ric Flair pleaded with the WWE Universe to put him in a steel cage match against Triple H at Taboo Tuesday 2005. The Nature Boy got his wish and the Intercontinental Championship was on the line.
The prestigious Intercontinental Championship was a prop in their feud. Nevertheless, it didn't take the drama away from this violent match, and Naitch emerged victorious against his former friend.
9 Jeff Hardy
The winner between Triple H and Jeff Hardy's number one contender match for the WWE Championship would face Randy Orton for the title at the 2008 Royal Rumble.
Triple H was the overwhelming favorite to prevail, and this was the beginning of Triple H and Jeff Hardy's excellent run of matches against each other. Ultimately, the Rainbow-Haired Warrior pick up the upset win at Armageddon 2007.
8 Sheamus
Triple H and Sheamus collided in a Street Fight at Extreme Rules 2010 with the Celtic Warrior looking for revenge after he lost to the Game at WrestleMania 26. Sheamus was the aggressor throughout the match.
Sheamus employed his physical style in the match, but the Game was not to be denied. He was defiant but it wasn't enough as Sheamus connected with multiple Brogue Kicks to beat Triple H who was carried out on a stretcher and written out of storylines for almost a year.
7 The Undertaker
Triple H and The Undertaker are two of the biggest names to grace a WWE ring. The Phenom has beaten Triple H in several marquee matches on a premium live event.
In front of his hometown fans in Houston, Texas, he defeated the Game at WrestleMania 17. He retained the WWE Championship at King of the Ring 2002, and he beat Triple H in two more WrestleMania epics at WrestleMania 27 and 28 with the Hell in a Cell match at the latter.
6 Brock Lesnar
The trilogy between Triple H and Brock Lesnar was underwhelming considering the star power that both men possessed. The Beast Incarnate systematically decimated Triple H in their main event encounter at SummerSlam 2012.
Lesnar lost to Triple H at WrestleMania 29, and their decider was in a steel cage match at Extreme Rules 2013. Lesnar with a steel chair is a scary prospect and he unloaded some vicious chair shots on the Game en route to winning their feud.
5 Daniel Bryan
The curtain-raiser between Triple H and Daniel Bryan at WrestleMania 30 had a lot riding on it. The winner would join the WWE Championship match between Randy Orton and Batista in the main event.
Fans desperately wanted Bryan to prevail as he had been under a torrent of abuse from the Authority. The atmosphere was electric, and Bryan booked his spot in the main event of WrestleMania 30 by overcoming Triple H in a hard-fought battle.
4 Roman Reigns
The main event between Triple H and Roman Reigns at WrestleMania 32 was met with a chorus of boos. The Game's WWE Championship was on the line, and the match was slow and podded on.
The result was inevitable that Reigns would recapture the WWE Championship from Triple H. Moreover, Reigns was shoved down fans' throats and they were not ready to accept him as the next face of the company.