The legacy of Triple H is ultimately a confusing one. There are few who would disagree that at his peak, he may have been the absolute best wrestler on the planet for an extended period of time, having spectacular matches with anyone you could name. In addition, once he moved into semi-retirement and became deeply involved in the business side of WWE, he became lauded for his work with projects such as the NXT developmental program. However, there were also portions of his career where he pretty much openly used his backstage power to further his career at the expense of other talented wrestlers, which earned him an incredible amount of ire among sections of the fanbase. Ultimately, while Triple H is undoubtedly a legendary figure in the wrestling business, he may never truly get the full recognition of how good he really was over his career. So, we’re aiming to change that perception for the better, with this list of the absolute best matches (and there were many) of Triple H’s long and legendary wrestling career.
15. vs Taka Michinoku, Raw, 2000
For all the (somewhat legitimate) negativity people began throwing at Triple H in the latter stages of his career, there was an extended period in 2000-2001 where he probably had a really good claim on being the best wrestler in the world. Suffice to say, you’ll see a lot of his work from that time frame on this list, starting with this completely unexpected classic match that many people point to when they talk about how absolutely on fire Triple H was as a worker at the time. What looked like a complete squash match against talented but horribly underutilized Japanese wrestler Taka Michinoku ended up as a ridiculously great match, where even though Taka never truly had a chance of winning, the match was so well wrestled and had just enough outside influences that at several points, it actually seemed like he might upset the WWE Champion. This was the match which opened a lot of people’s eyes to Triple H’s strong wrestling abilities even when he wasn’t working with similarly high-level opponents.
14. w/HBK vs Legacy, SummerSlam 2009
While the D-Generation X reunion tour in the late 2000’s was largely criticized for being a blatant merchandising money grab instead of anything that would actually make the on-screen product better (a fair criticism, because they basically said that’s what it was at every opportunity), it did have at least one feud that led to some pretty great matches. Former Triple H protege Randy Orton assembling a group of second and third-generation wrestlers in a stable that was probably intended to elevate everyone involved, but really only ended up giving Orton disposable henchmen. However, when the team of Ted DiBiase Jr and Cody Rhodes set their sights on the “old guard” of D-X, the matches that followed were actually pretty incredible, featuring two young, hungry heels doing everything they could to outsmart two of the wiliest veterans in the business, and occasionally succeeding. Probably the best match between the two teams happened at SummerSlam, a straight-up tag match that saw the four put on an excellent display of tag team wrestling that occasionally gets forgotten about in the world of WWE. Future matches would get lost in overbooking and gimmicks, but the initial one, which saw Legacy pull out a shocking victory, made people believe that there was actually a great future ahead for DiBiase and Rhodes. Well, they were partially correct, anyway.
13. vs Chris Jericho, Last Man Standing, Fully Loaded 2000
We told you 2000 would be well-represented on here. A lot of ink has been spilled about the allegedly contentious relationship between Chris Jericho and Triple H, both in and out of the ring, and to be sure, over their careers, Triple H ended up with the upper hand and the victory pretty much every time they faced off. But no one can deny the chemistry Y2J and HHH had when they stepped into the ring, which first came to the forefront in this incredible Last Man Standing match that was the first real chance for Jericho to shine at the main event level since his debut. The list of truly good Last Man Standing matches is short indeed (repeated ten-count spots tend to suck the momentum out of even good matches), but this one almost certainly sits atop it, due to a combination of great wrestling, well-planned false finishes, and a hot ending that saw Triple H snatch victory from the jaws of defeat at the absolute last half-second. Some were disappointed that Jericho didn’t get the victory to catapult him into the main event for good, but looking back at his career, he ended up doing pretty well for himself anyway.
12. vs Batista, Hell in a Cell, Vengeance 2005
Triple H often gets accused of never “putting over new talent”, and in some cases that’s fair, but as you’ll see in this and other examples on this list, Triple H actually put over quite a lot of people in his career. And nobody can ever say that he didn’t do everything he could to put over Batista during the Animal’s rise to prominence, losing cleanly to Big Dave in three straight World title matches on Pay Per View, beginning with WrestleMania 21 and ending with this classic Hell in a Cell encounter at Vengeance. Not only did Triple H lose, he made Batista look like an absolute beast in all three matches, especially this final one, which had all the trimmings people expected from a Hell in a Cell match, and finally made people realize that Triple H actually wasn’t going to “get his win back” from Batista any time soon (or ever, as it turned out, as Batista was drafted to Smackdown immediately afterwards). These matches turned Batista from a silent bodyguard who started to get a fan following into a bonafide main event Superstar, and it’s in large part thanks to the work done by Triple H.
11. vs Cactus Jack, Hell in a Cell, No Way Out 2000
The match which led to the retirement of Mick Foley (well, it was supposed to, anyway), it built on their Royal Rumble encounter and threw a large, dangerous element into the mix in the form of the infamous Hell in a Cell stipulation. The idea was that Foley (in his Cactus Jack persona) would be more at home inside the Cell, which ignored the fact that he hadn’t won either Hell in a Cell match he’d been in, but to be fair, at least he had experience on his side. While it was going to be nearly impossible to top their Rumble match, or deliver on Foley’s insane promises involving leaping off the Cell without crippling him, they certainly gave their best effort, playing into the events of the infamous Mankind-Taker Cell match in order to raise the stakes and create an incredible visual spectacle for the finish. In the end, Triple H won and ripped the hearts out of Foley fans everywhere, but at least his in-ring career ended on an incredible match. For three whole weeks, at least.
10. vs Shawn Michaels, Raw, 2003
Roughly a year and a half after his miraculous return to the ring, which was initially thought to be a one-time thing, Shawn Michaels was comfortably ensconced as a regular wrestler on WWE programming. While in real life, Michaels had little to no interest at being World Champion, even allegedly turning down the opportunity on several occasions (he rarely worked house shows, which he would have needed to do as Champion, and may have worried that trying to carry the company would cause him to slide back into old, destructive habits), that didn’t stop him from having several incredible title matches. This one, which took place literally on the last Raw of 2003, came out of practically nowhere, as HHH and HBK, having reignited their rivalry, were given basically the entire second hour of a holiday episode for a match, and simply blew away everyone’s expectations with an instant classic. The only thing that hurt the match was a screwy finish that ended in a draw, after the audience thought Michaels had picked up a shocking victory and the World title, but there was very little not to like about it otherwise. Unfortunately, they would attempt to top themselves several times in the ensuing months, never coming close to reaching that peak again.
9. vs Daniel Bryan, WrestleMania XXX
As long and boring as the Authority’s reign over WWE was, when it came time for Triple H to get his comeuppance against the one guy he’d tortured more than anyone else, he went all out. The opening match of the 30th WrestleMania featured Triple H taking on Daniel Bryan in a match where the winner would be inserted in the main event match for the WWE World Heavyweight Championship. Surrounded by an audience that still didn’t quite believe that Bryan would actually get his deserved shot in the end, Triple H went out and put over Bryan in every way he possibly could, selling his offense like he’d been shot by a cannon, expertly working the crowd into a frenzy with his heelish shenanigans, and in the end, losing cleanly in the center of the ring to Bryan’s running knee finisher. While Bryan was already an overwhelming fan favorite going into the match, Triple H made Bryan look like a massive star in their match, giving Bryan all the momentum he would need for his emotional victory later that night.
8. vs Chris Benoit and Shawn Michaels, WrestleMania XX
This match doesn’t get talked about anymore, for obvious reasons, but at the time it was considered one of the greatest WrestleMania main events in history, as well as the just reward of a man who had been seen as hugely underrated by the companies he worked for in his career. While many complained about Shawn Michaels horning in on Benoit’s rightful one-on-one match, adding HBK gave the match an extra dimension (one which WWE would exploit for the rematch a month later, which took place in Benoit’s hometown of Edmonton, Alberta, Canada), and more importantly, another excellent wrestler in the mix. As one would expect when talking about all three man, the match featured incredible wrestling, and built perfectly to Benoit’s ultimate triumph on the grandest stage. Frankly, we wish this match could be held up more often as an example of good booking, great storytelling, and fantastic wrestling. Unfortunately, it can’t be, and it never will be.
7. vs The Undertaker, WrestleMania X-7
As much as WWE would try to sell their future WrestleMania matches a decade later as epic confrontations, in our eyes, those matches still failed to top the quality of their first Mania encounter, at what is considered by many to be the greatest WWE PPV in history. This match had literally zero expectations going in, as neither man had a direction and were thrown together thanks to other plans falling through at the last second. However, as we mentioned before, Triple H was still in that period where he was an incredible wrestler who could carry even mediocre talent to a good match (one which, sadly, was only weeks away from ending, although obviously nobody knew that at the time), and The Undertaker was starting to realize that his American Badass character meant he didn’t have to wrestle like a shambling zombie. The result was a wild brawl between two veterans that would have stolen the show at any other Pay Per View, but was probably only the third or fourth-best match at this one (which, for WrestleMania X-7, is not an insult at all).
6. vs The Rock, Ladder Match, SummerSlam 1998
More than anything, this was the match that put both men on the map, moving them from leaders of midcard stables to Superstars on the verge of the main event. D-Generation X and The Nation of Domination had battled it out for a while (including the infamous “D-X Dresses Up As The Nation” parody), and while a 2/3 Falls Match the previous month had been fairly disastrous due to an over-reliance on run-ins and decidedly bad booking, this match took those flaws and massively improved on all of them. For example, there were still run-ins, but not a ludicrous number of them, and they were handled in a way that did not detract from the action. More importantly, Rock and Triple H both wrestled the best match of their career thus far, setting the stage for even greater future success, as both would win their first WWE Championship within the next year.
5. w/Steve Austin vs Chris Jericho and Chris Benoit, Raw, 2001
Considered by many to be one of the best matches to ever happen on Raw, the quality of this match has been overshadowed both by Chris Benoit’s future actions, and the massive quad injury Triple H suffered at the very end of the match, derailing his career for the rest of the year, as well as the direction of WWE as a whole, and when he returned, his wrestling skills had slipped, ending his streak of dominance where he wrestled many of his best matches. But as for the match itself, it is the very best of tag team wrestling, between four of the best wrestlers on the planet at the time, all of them at the top of their game. It was considered the moment when both Benoit and Jericho made it to the top of the mountain and became main event talents in WWE (although due to complications, their true ascensions wouldn’t really happen until months later), and set the stage for what was expected to be a messy break-up between Austin and Triple h, leading to a feud that was planned to carry the summer months. Unfortunately, Triple H’s injury changed all of that, leading to WWE moving ahead with the WCW Invasion well ahead of schedule, and the rest is history.
4. vs Shawn Michaels, Unsanctioned Match, SummerSlam 2002
In what was originally intended to only be a one-time return for HBK, he and his best friend Triple H set out to make sure it would be one to remember (although we’ll say as little as possible about the ridiculous booking that led up to it, though, as Triple H turned on Shawn during an attempted D-X reformation, then Shawn was attacked by a mysterious assailant, who Triple H vowed to find, and it turned out to be…Triple H). They basically beat each other from pillar to post for a good long time, and while Shawn got the feel-good victory, Triple H had the last laugh when he hit HBK right in the surgically repaired spine with a sledgehammer. This was almost certainly Triple H’s best match since returning from his quad injury earlier in the year, but also has horrible memories as being the beginning of his two-year reign of terror over Raw, as he was awarded the World Heavyweight Championship shortly after this match and began squashing all competition to his position immediately thereafter.
3. vs The Rock, Iron Man Match, Judgment Day 2000
Some prefer their straight-up one-on-one fight (well, as one-on-one as matches got in the Attitude Era) at Backlash, but for us, it’s the Iron Man Match that really stands out, especially since it represents such a diametrically opposite sort of match when compared to another classic, the Bret Hart-Shawn Michaels Iron Man Match from WrestleMania XII. While that match had only a single pinfall, this match had nearly a dozen, as the entire match was the best parts of the combination of good wrestler and unbridled chaos that would mark the Attitude Era. It also included several clever spots, including Triple H intentionally getting DQ’d (giving Rock a fall) for clobbering Rock with a chair, then regaining his lost advantage by earning consecutive pins on his semi-comatose opponent. Heck, it even saw Rock get a pinfall with the ridiculously convoluted “La Magistral” cradle pin! The finish, which saw The Undertaker return in the debut of his “American Badass” character, might have set the record for highest number of crazy things to happen in the last few minutes of a wrestling match, and that’s not an easy bar to clear.
2. vs Steve Austin, 3 Stages of Hell, No Way Out 2001
This was, allegedly, supposed to be the ultimate payoff for Triple H paying Rikishi to run down Steve Austin at Survivor Series 1999, but more importantly, it was three matches rolled into one, between two of the very best wrestlers on the planet, right around the absolute peak of the Attitude Era, with WrestleMania X-7 just around the corner. For those who don’t remember, the first fall was a straight wrestling match, the second one was a Street Fight, and the third was inside a Steel Cage. Each fall was non-stop action from start to finish, with the trademark brawling style popularized by Austin mixed with the underrated technical skills of both men. Ultimately, Triple H would defeat Austin, which actually means that Stone Cold never truly got revenge on the man who had him run down, but then again, he was just about to main event one of the biggest Pay Per Views in WWE history and win the WWE Championship, so he made out okay.
1. vs Cactus Jack, Street Fight, Royal Rumble 2000
Honestly, this gets the top spot due to personal sentiment and a love of Mick Foley, so if you want the Three Stages of Hell match up here instead, feel free to make the switch in your mind. But for our money, this was the best (non-Rumble) match we’ve ever seen at the Royal Rumble Pay Per View, and one of the best Street Fights in wrestling history. It’s made even more impressive by the fact that Triple H basically got stabbed by a gigantic shard of wood mid-way through the match and didn’t miss a beat despite having a large puncture wound dripping blood down his leg. Even the booking leading up to the match, including the fantastic “reveal” of Cactus Jack, was spectacular, and the match was full of both great wrestling and fun call-backs to brutal Foley matches from the past (such as the handcuffs from the ’99 Rumble and the thumbtacks from Hell in a Cell). This is generally accepted as the match which “made” Triple H into a main eventer, and it’s hard to argue with that statement, as this would kick off nearly a year and a half of absolutely spectacular featured matches from The Game, many of which are also included on this list!