10 Triple H Matches That Made Him The WWE Legend He Is Today

When wrestling fans gather around the Internet forums and debate about the G.O.A.T.s — in polite and calm discourse, of course — many names are cited as the potential best ever. Performers such as "The Heartbreak Kid" Shawn Michaels, Bret "The Hitman" Hart, "The Nature Boy" Ric Flair, and "Macho Man" Randy Savage are the usual suspects in these conversations, but not enough love is given to "The Game" himself, Triple H. Perhaps it's because he married the boss' daughter and people believe he used his political clout to get ahead in the business, but there's no disputing the Cerebral Assassin could go in the ring. He never sat on his laurels or dialed it in, as he shared the ring with countless legends and more than stood his ground.


However, there are a select number of bouts of his that can be deemed unforgettable and game-changing for The Game. In some instances, he came out on top when the bell rung, while other times resulted in him doing the job for his fellow workers and helping to elevate the storylines. What's clear from Triple H's matches throughout the decades is that he certainly understood what was best for business, even when it meant him taking the L. So let's grab the magical water bottle, do the famous entrance pose or a crotch chop or two, and revisit Triple H's greatest hits. It's time to play the game!

Triple H vs. The Rock at SummerSlam 1998

The year 1998 was an important one for the then-WWF. Bret Hart was gone, Shawn Michaels had retired from a back injury, and many superstars from the years prior had jumped ship and sailed on down to WCW to make snow angels with Turner money. "Stone Cold" Steve Austin stepped up to grab the brass ring and become the guy in the company; however, there was a need for more stars to challenge him and move up to the main event scene. Two of the hottest young guns at the time were Triple H and The Rock. Previously, they had feuded as members of D-Generation X and The Nation of Domination respectively, but the time had arrived for them to elevate to the next level.


While the main event for SummerSlam 1998 was Austin versus The Undertaker for the WWF Championship in a no-DQ match, it was The Rock and Triple H's Ladder Match for the Intercontinental Championship that stole the show. The performers put their bodies on the line to deliver a classic back-and-forth match in the same vein as the legendary ladder bouts between Michaels and Razor Ramon years earlier. The crowd in attendance got behind them, almost forgetting who was the heel and who was the babyface, as they showed respect for the high-caliber performances on display. In the end, Triple H emerged victorious, but this match served its purpose: to announce both men's arrival as the future.

Triple H vs. Cactus Jack at Royal Rumble 2000

ECW had a profound impact on the wrestling industry. It took hardcore wrestling and made it mainstream, as the audience wanted to see more blood spilled than a "Rambo" film. WWF took note of this, as the poor Spanish announcers' table became the victim in all the anarchy and chaos. Yet, no one expected the promotion to push the boundaries too much. A bit of blading here and there? Sure. Maybe a kendo stick and chair shot, too.


However, Triple H and Cactus Jack decided to put on one of the bloodiest bouts in the company's history at Royal Rumble 2000. Billed as a Street Fight for the WWF Championship, this wasn't the type of brawl on the asphalt where people trash talk and throw wild haymakers that trip them over their own feet and become meme fodder. No, this was a bruising brawl that took a toll on the pro wrestlers' bodies and spilled crimson all over the mat.

At one point, Cactus took out the infamous thumbtacks, and this wasn't to help The Game put up posters of himself on the wall. It was quite the sight to see the men's bodies covered in the thumbtacks, while Triple H delivered a Pedigree to Cactus on top of the carnage to retain the championship. It was a bloody, brutal match that could possibly only have been topped by Too Cool's dance in the middle of the Rumble match that same evening.


The Elimination Chamber Match at Survivor Series 2002

By 2002, Triple H had established himself as the main draw in WWE. "Stone Cold" Steve Austin had retired, while The Rock was starting to solidify himself as the most electrifying man in Hollywood. For that year's Survivor Series, there needed to be something more; higher stakes to draw the buy-rates and to get the crowd pumped. The solution was the inaugural Elimination Chamber match — supposedly the most unforgiving and punishing structure ever created. Participating in the Devil's Playground for the World Heavyweight Championship was Rob Van Dam, Chris Jericho, Booker T, Kane, Shawn Michaels, and Triple H. The odds were always against the champion from the start, but that's exactly what the audience wanted to see, since The Game had become one of the most despicable heels around, especially after the horrendous Katie Vick angle.


In the end, there were two men left in the Elimination Chamber: Michaels and Trips. The two had endured a tiring and highly physical contest, leaving both men gasping for air and trying to get a second wind. No one had a clue who would win since they were so equally matched. Ultimately, Michaels popped up with a little Sweet Chin Music, pinning his former best friend for the belt and completing his legendary comeback after four years away from the ring. It was the right result and a feel-good moment for Survivor Series, even if Michaels dropped the title back to Trips a few weeks later.

Triple H vs. The Rock at Judgment Day 2000

The Rock and Triple H had one of the most iconic rivalries in pro wrestling history. They stood across from each other in the ring so many times that they probably communicated via ESP. When Judgment Day 2000 rolled in, they had both been champion in that calendar year and faced off a couple of times already. However, none of the bouts had been quite as spectacular as what was to come on that evening. The Rock and The Game were locked in a gruelling 60-minute Iron Man contest for the title, and refereeing the match was someone who knew a little something about this kind of contest: Shawn Michaels.


While Michaels and Bret Hart's infamous Iron Man match at WrestleMania XII ran into sudden death and only had one decision between the men, The Rock and Trips decided to exchange their fair share of pinfalls, submissions, DQs, and count outs within the time limit. Surprisingly, HBK also called the contest down the middle, never showing favoritism to any performer. The match ended with Triple H picking up six victories to The Rock's five, with the final decision coming after The Undertaker attacked Trips with only seconds to go on the clock. While this Iron Man match doesn't get as much praise or love as the WrestleMania XII one, it had the audience on their feet as both men pushed each other to the limit.


Triple H vs. Chris Benoit vs. Shawn Michaels at WrestleMania XX

No one can accuse WrestleMania XX of trying to take shortcuts. It was a long show consisting of 12 matches. While most fans tend to remember it for the infamous match between Brock Lesnar and Goldberg, which saw both men booed out of Madison Square Garden, there were other colossal contests that live on in the memory for the right reasons. Eddie Guerrero's title defense against Kurt Angle remains a classic for lovers of technical wrestling, while the triple threat main event between Chris Benoit, Triple H, and Shawn Michaels was chosen by IGN – and many others — as one of the best WrestleMania matches of all time.


Benoit had been in the WWE for four years at that point, after having jumped ship from WCW, along with Eddie Guerrero, Perry Saturn, and Dean Malenko. While Guerrero had gone on to capture the gold, there was still a doubt from fans if the WWE would put the big one on Benoit, who was a smaller performer. Pitting him in a match with Michaels and Triple H — two of the most decorated champions in pro wrestling history — instantly put him at a disadvantage. The contest featured close shaves and frenetic finishers, as the men fought for over 24 minutes before Benoit forced The Game to tap out, claiming the World Heavyweight Championship. While Trips was on the receiving end of the loss here, his work in the match was highly praised.


Triple H vs. The Undertaker at WrestleMania XXVIII

The Game and The Deadman were no strangers to facing each other at WrestleMania. Yet, the bout between the two at WrestleMania XXVIII felt that extra bit special, even aside from The Streak being on the line. It was the second consecutive time that Triple H and The Undertaker were squaring off at 'Mania after The Deadman had retired Shawn Michaels two years earlier. This time, though, they would clash in a match that both wrestlers had become renowned for: Hell in the Cell. To make it even juicier, Michaels would be the special guest referee. Instantly, alarm bells rang, as everyone feared Michaels and Triple H would conspire to cost 'Taker his unrivaled streak of victories. For the first time ever, it appeared as if The Undertaker was at an early disadvantage in a 'Mania match.


Michaels toyed with calling the match down the middle before he inevitably became involved in a significant way, and hitting 'Taker with some offense. There was a genuine moment when The Game covered his opponent and everyone believed it was over. It wasn't to be, though, as The Undertaker pulled out all the stops and overcame the overwhelming odds to win the clash. The audience at the Sun Life Stadium clapped for all three men on their way to the back, as everyone recognized this 30-minute bout for being one of the best and most emotionally charged contests they had ever seen.

Triple H vs. Chris Jericho at Fully Loaded 2000

One of the most underrated rivalries in WWE history is the one between Triple H and Chris Jericho. From the moment Y2J walked into the company as the Millennium Man in 1999, he was thrust into a bitter feud with The Game as they traded barbs and fists on regular programming. At times, the title was involved in their battles, but one of their better contests was nothing more than a grudge match when it was only their pride at stake. The Last Man Standing bout at Fully Loaded 2000 allowed the wrestlers to take out their frustrations on each other in a highly physical encounter for a little over 23 minutes.


It was a tight contest that featured interference from Stephanie McMahon-Helmsley regularly, but The Game managed to get to his feet by the nine count, beating Jericho by a single second. While it wasn't the result Y2J was looking for, it's arguable this is the match that made the WWE take him seriously and realize he had the potential to be a main event superstar. Triple H ensured his opponent looked good, allowing Jericho to get in his moves and letting the audience believe there was a chance Y2J could come out triumphant. A year later, Jericho won the big one.

Triple H vs. Brock Lesnar at WrestleMania XXIX

The best kind of matches are the ones with a lot at stake. At WrestleMania XXIX, Triple H faced Brock Lesnar in a No Holds Barred contest with the stipulation that if The Game lost, he would need to call time on his in-ring career. Considering how Triple H had already started transitioning to an office role in the WWE, there was the thought this could be his last hurrah in the squared circle. It also didn't help that he had a rotten record against The Beast Incarnate, who looked nigh unstoppable at this point in history.


The contest didn't start in the right way for Triple H, who suffered second-degree burns from the pyrotechnics during his entrance, as per Yahoo. However, he didn't let that get in the way, as he had a score to settle with Paul Heyman's number-one guy. It was a proper slugfest as the two titans exchanged blows and hard-hitting moves, while Shawn Michaels got involved on behalf of Hunter and Heyman squirmed around on the outside in typical fashion. Triple H picked up the victory after he hit Lesnar with a Pedigree on the steel steps. While it might not have been the prettiest match in WrestleMania history, it showed that Hunter could brawl with the best of them.

Triple H vs. Shawn Michaels at SummerSlam 2002

After four years away from in-ring competition, Shawn Michaels returned to the squared circle for an unsanctioned match against his former friend and D-Generation X co-founder, Triple H. For the fans, HBK was the returning darling — a fan-favorite performer who had to take a break from the business due to a bad back and a lost smile. In the other corner was Trips, the person who had stepped up and took Michaels' spot as the king of kings. More importantly, there was the elephant in the room: Could Michaels still hang with the best after all this time away?


While Triple H lost the fight, he helped Michaels get his mojo back in the process. They convinced the audience there was real heat between them, making everyone believe this was a dangerous scenario when it was anything but. It's clear to see that Trips was the only person HBK trusted with his return, since he took extra care of him in the ring. They had a safe and sound match, helping to persuade Michaels that he still had it and could easily go at the highest level. In many ways, WWE fans owe The Game a special thank you for playing a crucial role in HBK's comeback.

D-Generation X Vs. The Nation at Over the Edge 1998

Tony Khan and AEW may love trios matches more than life itself, but in 1998, they were fairly rare to witness on wrestling programming. However, at Over the Edge, there was a memorable three-man tag clash between Kama Mustafa, D'Lo Brown, and Owen Hart of The Nation and Triple H, Billy Gunn, and Road Dogg of D-Generation X. This bout isn't often mentioned or remembered by the average fan as one of the greatest matches of all time; however, it was an excellent display of three-man tag wrestling and a nice feather in the cap for the Nation and D-X's late '90s feud.


As the penultimate match on the card, the clash had a lot to do, since the previous matches on the night hadn't been five-stars by any means. Yet, Trips and the rest of the boys put on a fun match filled with the expected spots and riffs between the two factions. The Nation came out tops in the end after Hart hit Triple H with the Pedigree, but the result was inconsequential. The crowd had a good time, as these two factions managed to save a fairly rotten show from being a complete flop. Also, it showed that The Game wasn't only a talented singles star, but he also knew how to participate in multi-competitor matches.