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Triple H’s first WWE title win is just one of his many in-ring highlights/Credit: WWE.com
August 23 marks the anniversary of Triple H’s first WWE Championship victory, a moment that ignited a main event run that would see him tangle with the best the industry had to offer over the course of two decades.
It was also the moment that solidifed his status as a top star in a business he had devoted his life to and was determined to make his own.
Leading to that signature win, and in the years that followed, The Game would be responsible for some of the greatest and most memorable in-ring moments in WWE history. From classic matches to unforgettable feats of toughness, he would ensure his legacy as a performer was emblazoned in the minds of anyone who watched him work.
In celebration of his first title win in 1999, these are the 10 greatest in-ring moments of Triple H’s career, ranked on historical significance to WWE and personal importance to the wrestler himself.
1 of 10
The rivalry between D-Generation X and The Nation dominated the summer of 1998 and led to the rise in prominence of the faction leaders, Triple H and The Rock.
Their battles over the Intercontinental Championship culminated at SummerSlam with a brutal ladder match for the coveted title.
The bout relied heavily on the drama of the climb, the storytelling that incorporated the likes of Mark Henry and Chyna into the finish, and the unbridled physicality that left The Rock bloodied and Triple H selling a knee injury that ultimately proved to be more realistic than most knew at the time.
In the first real display of his toughness to that point in his career, The King of Kings overcame a knee issue and capitalized on late interference from Chyna to regain a title he had lost a young Rocky Maivia in February 1997.
The match was a breakthrough performance from Triple H, who had long been a good hand in the ring but needed that one contest to really break out and prove he had the ability to be a main event performer.
The Rock may have had a more immediate rise, but The King of Kings was well on his way to accomplishing all that he wanted.
2 of 10
There is a prevailing sense that, at the height of his run at the top of WWE, Triple H did not want to put others over.
While there is certainly a track record to support that, mostly in a year-long stretch from 2002-03, the argument falls apart when you hit that midway point of the decade.
He was integral in helping elevate Chris Benoit as world champion in 2004 and firmly established Batista as a main event star for the company a year later.
Look no further than Vengeance 2005 and the main event for the World Heavyweight Championship inside Hell in a Cell. The trilogy between mentor and protégé culminated with one of HHH’s greatest matches.
When the referee’s hand slapped three, it was Triple H staring up at the lights, with his goal to put Batista in a position to lead the company through the next five years complete.
It was a selfless performance, one that even saw him take a wicked powerbomb on the ring steps to emphatically end his title chances and really made a star out of a guy who had previously been seen as the “other guy” in Evolution.
3 of 10
As American blueblood Hunter Hearst Helmsley, Triple H was originally slated to win the 1996 King of the Ring until an infamous embrace in the middle of the ring at Madison Square Garden earned him a year-long punishment that included doing jobs for just about anyone on the roster.
By the time June 1997 rolled around, Vince McMahon apparently decided that his future son-in-law had learned his lesson because Helmsley was entered into that year’s tournament. And two wins over Ahmed Johnson set him up for a battle with Mankind in the finals.
With the assistance of Chyna, he would defeat a man against whom he would have many battles in the years to come, but the win signified more than the start of a rivalry or the beginnings of a push.
It was redemption for Helmsley, who proved he had the “thick skin” necessary to take everything thrown his way in the year leading to that moment and regain the trust of his employer.
The moment was the culmination of a journey back to relevance, something he likely felt he had fallen out of as he served his penance for the so-called “Curtain Call” on Scott Hall and Kevin Nash’s last night with the company a year earlier.
4 of 10
Prior to 2000, a heel had never left the main event of WrestleMania with the WWE Championship.
Even in 1993, when it appeared as though the ninth incarnation of the event would go off the air with Yokozuna standing tall, the decision was made to put the strap on Hulk Hogan and send the fans home happy.
As WWE embarked on a new century, though, it wanted to change things up. Enter, Triple H.
The Game had become the most hated man in professional wrestling, a top heel with a penchant for extraordinary in-ring performances and the character around whom WWE television was built. He was the best in the business and had the in-ring output to prove it.
It is no surprise Vince McMahon would have felt comfortable making the call for Triple H to retain, following a shocking swerve by The Chairman of the Board, of course. He knew The Cerebral Assassin was as hot a bad guy as he had promoted in years and fans would likely spend another whopping $40 to purchase Backlash to finally see The Rock unseat him for the title, so he did the unthinkable.
Triple H defeated Rock, Mick Foley and Big Show to retain his title, and the fans in Anaheim let McMahon know how unappreciative they were for that particular finish.
Fan sentiment ensured it would be another 15 years before a heel stood tall to close out the biggest pay-per-view of the year, but it is a testament to the character The Game had created that he was even in a position to etch his name in the history books the way he did then.
5 of 10
In every wrestler’s career, there is one match that makes them in the eyes of the fans. It serves as the exclamation point to all of the booking and the strong push from management that has gotten a particular name to that point of the career, justifying the trust the bosses have in a particular worker.
For Triple H, that contest was a Street Fight against Cactus Jack at the 2000 edition of the Royal Rumble.
The Game had been on a meteoric rise, taking the ball handed to him in the summer of 1999 and running with it. He had married the boss’ daughter in an unforgettable wedding angle, sent Vince McMahon away from television with a win over him the previous month and had developed into the centerpiece of the WWE product.
But he still needed that one performance that forced the audience to accept him as one of the undisputed top dogs in the business. He got it in the form of a brutal match with a vengeful Jack, who unleashed two months’ worth of frustration and anger over his treatment at the hands of the power-hungry bad guy.
There were thumbtacks, barbed wire and even an appearance by The Rock, who saved his on-screen buddy from a violent assault by Triple H. In the end, though, it was the heel who emerged victorious after a sickening Pedigree into the aforementioned tacks.
A five-star classic that earned instant acclaim, the match was the moment when Triple H went from being a guy WWE hoped would be the top villain for the foreseeable future and definitively staked his claim to that title.
6 of 10
By 2016, Triple H was rarely competing between the ropes, instead enjoying life away from the ring as one of the most influential men in the industry.
However, an opportunity to come back and work with Roman Reigns in the main event of WrestleMania 32 was enough to coerce him out of semi-retirement and back to the squared circle, beginning with the men’s Royal Rumble match in January.
With the WWE Championship at stake, Reigns survived from the No. 1 spot in the match all the way to the end, only for Triple H to reveal himself as the final entrant.
Taking advantage of a distraction by Sheamus, Triple H dumped The Big Dog to the floor to end his reign as champion, then overcame Dean Ambrose to win the match and the title.
Some 21 years after he debuted for the company, The Game won what would be world title No. 14, the last of his career. It was a triumphant moment, greeted with a thunderous roar, that set up one last ‘Mania main event and won over fans who were just happy to see anyone but Reigns leave with the title.
7 of 10
The Iron Man match between Triple H and The Rock for the WWE Championship at Judgment Day 2000 had no right to be the classic encounter it was.
The Attitude Era was alive and well, and the fans of that time did not have the attention span to sit through 60 minutes of action when they were routinely getting four or five minutes of ring work per contest on Raw and SmackDown.
The Game and The Great One were hardly the two wrestlers anyone would look at as being able to put together an hour-long bout that kept fans interested, either.
The doubters were proved wrong, though, as they turned in what is, arguably, the greatest Iron Man match in WWE history and proof positive of their strengths as workers. Triple H was in the midst of the greatest in-ring run of his career, while The Rock’s charisma and energy helped pop the audience and keep them invested.
Their chemistry with one another did the rest.
A wild and enthralling match ended in controversy with the return of The Undertaker, and Triple H regained a title he had lost a month prior at Backlash.
In a year in which he did his best work, The Game’s performance in that 60-minute, drama-filled classic may well be his masterpiece.
8 of 10
John Cena suffered a neck injury in the fall of 2007 that forced him to the sidelines and put WWE in the difficult position of having to scramble to book an entire PPV, at the top of which Cena was meant to defend the WWE Championship against Randy Orton.
Triple H stepped in and proceeded to turn out one of the most incredible nights of his career.
First, he defeated Orton in a straight-up wrestling match to win the title. From there, he settled his feud with Umaga by defeating The Samoan Bulldozer in a Street Fight. Then, in the main event, he narrowly lost a Last Man Standing match that gave Orton the title back.
That is a lot of HHH on one broadcast and it never would have worked with a lesser wrestler. The Game, though, is every bit the cerebral performer he claims to be and was able to turn three matches, against two opponents, in one night into three totally different bouts that told three different stories.
The fans in Chicago ate it up, appreciating the efforts of The Game and his dedication to his craft. It is a testament to his work rate and his abilities between the ropes that the show did not flop spectacularly and put WWE in an even more difficult situation than it was without its top star for the foreseeable future.
Given how many times over the course of his career that situation played out, where he was relied upon to step up and deliver, it is no wonder Triple H was presented at the top of the card for as long as he was.
9 of 10
Over the course of his career, Triple H has had insults hurled in his direction and claims of backstage politicking attempt to undermine his work but no matter who said what, there was one thing no fan or critic could deny: He was tough.
The May 21, 2001 episode of Raw concluded with The Game teaming with “Stone Cold” Steve Austin to defend the WWE Tag Team Championships against Chris Jericho and Chris Benoit in what was slated to be the start of a huge rivalry that would end at King of the Ring.
Late, Triple H entered the squared circle to break up a Walls of Jericho on Austin but when he planted his right foot to push off, he tore his quadriceps muscle, producing a shooting pain down his leg.
Most would have crumbled to the mat and refused to move. Instead, he was intent on finishing the match. To do so, he would endure the painful Walls on the announce table. The same leg in which he had just torn the biggest muscle in the body was now the focal point of Jericho’s finishing move.
Again, no one would have faulted the man for lying on the table and calling it a night given his condition. Instead, he limped back to the ring, entered and blasted Austin with a sledgehammer to set up the finish.
Here was a guy who was in the middle of the greatest run of his career, who just suffered this devastating injury but was determined to wrap things up as expected. He did and earned a ton of respect from fans and his peers in the process.
Over the years that followed, he would endure other significant injuries and continue right on in the best way he knew how.
10 of 10
You never forget your first.
Triple H added the first of 14 world titles to his career on August 23, 1999 with a win over Mankind in the main event of WWE Raw.
Many expected it the previous night, when all of the company’s booking seemingly pointed at The Game defeating Mankind and “Stone Cold” Steve Austin in the main event of SummerSlam to win the title.
A surprise ending, in which Foley emerged with the title and was at the center of all the photo ops with Minnesota governor (and special guest referee) Jesse “The Body” Ventura, delayed his ascent to the top of the business.
It was OK, though, because a main event for the title on Raw meant more people would be watching than would have seen it on PPV. The Game would achieve his greatest moment in front of a worldwide audience by beating one of his greatest rivals and forever etching his name in history books alongside Hulk Hogan, Randy Savage, Bret Hart and Shawn Michaels.
A long, arduous climb to the top of the industry that saw him slipping and sliding in pig crap at the end of a midcard feud with Henry Godwinn, a year-long punishment for his role in the Curtain Call and the frustrating wait for his turn, culminated with him realizing his dream.
Would the moment have meant more on one of WWE’s more prestigious PPVs? Probably. Would it have been more historically significant? Sure, but that does not diminish a moment he had worked a decade to achieve.
His run would ultimately be short, thanks to some Vince Russo booking that left fans scratching their heads, but Triple H would be one of the industry’s biggest stars and ready to take it over by the end of the year.
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