The 30th April 2020 marks the 25th anniversary of HHH’s WWE in-ring debut! Yes, it’s been 25 years since Hunter Hearst Helmsley made his mark on the WWE. Who’d have thought he’d marry the owner’s daughter, become one of the most prominent main eventers in WWE history, and also reign as the company’s COO for a duration! Now, he tends to stay away from the ring, busy being WWE’s Executive Vice President of Global Talent Strategy & Development and head of NXT! At the time I started watching wrestling, 1999, the BIG STAR was Stone Cold, closely followed by The Rock…but HHH was on his way to being the BIG HEEL.

By late 1999/early 2000, he was my favourite wrestler in the company. Who doesn’t love a bad guy? And this guy had it all; the title, the girl (Stephanie McMahon, who I bloody adored in that era), the physique, and the in-ring prowess. With Stone Cold gone, he was the MAIN EVENT of 2000 (yes, even more so than The Rock!). Since then, I’ve fallen in and out of “love” with the guy, but he’s without a doubt one of the best.

(Click here for my Top 10 Worst Triple H Matches!)

And to celebrate his 25th anniversary, here are my Top 10 Greatest HHH Matches!

hhh 25 years replica title
Might treat myself to this replica belt!
  1. vs Jeff Hardy (No Mercy 2008, WWE Championship Match)

You read the same thing all the time: “HHH was only in it for himself, he rarely ever put anyone over.” To a degree, that’s true (just ask Booker T, or Rob Van Dam!), but from time to time, he’s made a few exceptions. Looking at the result of this match, you’d think this is an example of HHH burying a red-hot commodity (at the time, Jeff Hardy was beloved by fans, perhaps more so than any other point in his WWE tenure). However, even losers can sometimes shine brighter than the winner, and that’s no truer than this match. HHH did everything he could (well, apart from taking the pin!) to put Hardy over as a legitimate threat to his title. Hardy, perhaps at the peak of his wrestling ability as well as his popularity, poured his heart and soul into this cracking contest. The two together put on one of the best matches of that year, that was unfortunately overshadowed by the (overrated, in my opinions) main event Ladder match between Y2J and HBK. An under-appreciated match that deserves more love!

  1. vs Booker T vs Kane vs Rob Van Dam vs Chris Jericho vs Shawn Michaels (Survivor Series 2002, Inaugural Elimination Chamber, WWE World Heavyweight Championship Match)

In most cases, the original is always the best. There are few remakes and sequels out there that better the original. We can apply the same logic to wrestling as well. Take, for example, Inaugural Elimination Chamber match. There have been many after it, but few have reached the level of unpredictability and mayhem that the original entailed. You could argue that there were no duds in this Chamber match, a problem that daunted many later ones. All six wrestlers were among the top wrestlers of Raw at the time. HHH was the main component of this match, the champion, who’s there from the start of the bout til the end of the bout. He’s even on the receiving end of a nasty looking spot where RVD leaps onto him from the top of a chamber pod…but his knee lands on HHH’s throat! HHH and HBK are the last two men left standing, and that confrontation itself is worth watching.  Going into the match, no one really knew what to expect. Would the wrestlers fight on the steel floor outside? Would anyone dare climb atop the chamber pods and leap off onto a prone body? Were those glass doors really bulletproof?  Every other Chamber Match has used this as a template. It had everything: novelty, star power, drama, emotion, holy s**t moments and a feel-god ending…

  1. and Stone Cold Steve Austin vs Chris Jericho and Chris Benoit (Raw, 24/4/2000)

A tag team match on Raw, you say? Well, some of the best tag team matches of all time occurred on Raw. This put heel Austin and HHH against the red-hot babyface team of Chris Benoit and Chris Jericho. These four went hell for leather in a cracking main event, one of the best matches in Raw history. Of course, it’s largely erased from modern day WWE discourse because of Chris Benoit, but don’t let that put you off. Four of the best wrestlers on the 2000 roster go all out, bringing the best out of each other. You’ll also witness intense fortitude from HHH as he tears he quad late in the match and carries on, even withstanding the Walls of Jericho (I can’t imagine how much pain he must have been feeling!). This is the last great bout of the old HHH, before he came back from his injury a year later looking like The Incredible Hulk…and wrestling like Gene Snitsky.

  1. vs Undertaker (WrestleMania X-7)

What, you thought I’d include another HHH/Taker match from Mania’s 27 or 28? For my money, their first and best Mania match was at WMX-7, and the only reason it lays largely forgotten is because WMX-7 has even better matches on the card. Yes, WMX-7 is the finest Mania of all time, and this awesome match is only the fourth best on the card. There were no slow pauses for “drama” here, or HBK shoved into the match for “story” reasons. At the time, Biker Taker wasn’t known for his in-ring prowess (or his great ‘Mania matches), but he is on full throttle here. Just like the match, Taker rarely pauses for breath, instead going toe to toe with HHH in an intense brawl that never lets up until the end (and keeps you guessing as to who will win). Screw their other Mania matches; if you want non-stop action and excitement, this is their masterpiece.

  1. vs Shawn Michaels (Summerslam 2002, Unsanctioned Match)

hhh hbk summerslam 2002
They used to be best buddies…

At this point in HHH’s career, he was just taking up main event space. At the beginning of 2002, HHH had returned from the aforementioned serious quad injury in no.8 to a massive ovation. However, it was clear he had returned too soon (and too big!). He was not the wrestler he used to be. Most of his matches were boring. Could HBK, who had been out of wrestling for four years, put on a decent match against the lethargic HHH? Oh yes! The two put on one of the best Summerslam matches ever… The story told inside the ring was nothing short of brilliant. The old lion, HBK, had returned to fight a former friend who had turned against him. HHH, that former friend, wanted to cripple HBK, who had retired due to an injured back. Did HBK have what it took to fight ‘The Game’? HBK answered with a resounding ‘yes.’ From start to finish, HBK looked like his old self, bouncing around the ring and bumping like a madman. His initial flurry of offence at the start of the match was only a hint that he ‘still had it.’ But HHH is just as great here, playing the heel to perfection. It had a triumphant return by a wrestling great, a dominant heel performance, and a story that was told beautifully. One of the best Summerslam matches of all time!

  1. vs Chris Jericho (Fully Loaded 2000, Last Man Standing Match)

Yes, I was fully rooting for HHH in this bout. I enjoyed Jericho’s feud with Chris Benoit (who?), but Y2J still hadn’t struck a chord with me. But he made me take notice with this match. It had a great build, basically centring around Jericho calling HHH’s wife unpleasant names (a storyline that probably wouldn’t happen nowadays!) Who wouldn’t want to destroy a man who was continually calling their wife awful names? And the match lived up to the build. Some Last Man Standing matches feel disjointed, a bout of fits and starts that never quite clicks. This had a gripping story running through it and some great spots. It was the night that Jericho looked like he was a main event player. The match itself is one of the best Last Man Standing matches in WWF history.

  1. vs Chris Benoit vs Shawn Micheals (WrestleMania XX, WWE World Heavyweight Championship Match)

Yet another match that’s erased from modern day WWE discourse because it has Chris Benoit involved! But this is among the best main events of WrestleMania (at least in the Top 5, if not higher). HHH had been given the WWE World Heavyweight Championship by Eric Bischoff the previous year and had largely held it from that moment until ‘Mania. Unfortunately, he simply couldn’t go in the ring like pre-quad tear HHH, so when he wasn’t wrestling HBK, he wasn’t worth watching. Of course, opposite opponents like HBK and Chris Benoit, anyone would struggle to have a bad match, but HHH worked just as hard as both of them to produce an absolute blinder. Perhaps the fact that the rest of Mania XX was awful helped the main event shine, but in any context, it would be one of the great Mania main events of all time.

  1. vs Daniel Bryan (WrestleMania XXX, Winner Inserted Into Main Event)

This is second only to Bret v Owen at WMX in Top 10 WrestleMania opening matches. Possibly even more personal than brother v brother, this capped off a feud that started at the end of Summerslam 2013. HHH, in the guise of The Authority, had made Bryan’s life a living hell since turning on him at Summerslam 2013. I don’t have time to do into the real/fake stories of how Bryan came to WMXXX, but suffice to say the great underdog had one obstacle in his path to main eventing WMXXX: HHH. Whoever won this opening bout would be inserted into the main even against Randy Orton and Batista. The match that ensued was a technical masterpiece, showcasing a side of HHH that we’re not used to seeing. Of course, Bryan was on top form here, but at the spry age of 42, HHH was also on top form in what I reckon is his best Mania match ever. A sublime piece of work.

  1. vs The Rock, Judgment Day 2000 (Iron Man Match, WWF Championship Match)

Among my most-watched WWE matches, this must be up there. It is my favourite Iron Man match of all time (and has one of the best pre-match video packages ever. Watch it here ). It had one of the best heels against one of the best babyfaces. It was (sort of) the end of a feud that had lasted years. In some of these gimmick matches, the original is best. But here, the original was pretty dull. This is intense, rarely lets up, and had more than one pinfall! It’s paced to perfection, doling out the pinfalls to keep the audience invested. It has HHH utilising the gimmick to use a chair, earning himself a DQ but consequently earning 2 pinfalls over The Rock. By 55 minute mark, it’s neck and neck after a brilliant babyface comeback from The Rock, and the nail-biting begins! Oh, it also includes one of the best returns ever in the closing moments. Yes, I was a huge HHH mark in 2000/2001, and I re-watched this match on tape many, many times. It gets better each time I watch it!

  1. Vs Cactus Jack, Royal Rumble 2000 (No Holds Barred, WWF Championship Match)

hhh cactus jack

This is one of my all-time favourite matches. It  developed from  a believable and brutal rivalry between HHH and Mick Foley that really extended far back to 1997. HHH became a star and Mick Foley proved he could still put on a hell of a match after a relatively quiet 1999. He was more of a comedy act in 1999, teaming with The Rock and playing matches for laughs. Enter the most sadistic wrestler of all time…I think you know the guy…his name is Cactus Jack! So both wrestlers had something to prove at Royal Rumble 2000. HHH wanted a memorable main event, which had eluded him beforehand. Foley/Jack wanted to prove that he could still bring out the hardcore, sadistic wrestler within. What follows is one of the most brutal matches in WWE history.  Broken pallets, a barbed wire bat, handcuffs, chairs, thumbtacks…all of these are more are utilised in this “hellacious” bout.  Part brawl, part ECW hardcore match, this stands as HHH’s finest match. Their Hell In A Cell bout at the following PPV No Way Out 2000 was very good, but nothing could top their Rumble bout. It’s sometimes hard to watch, but viscerally thrilling. HHH would go on to have a great year and solidify himself as a main eventer  (and one of the all-time best heels). Mick Foley would retire and un-retire within the space of a month to be slotted into the WrestleMania 2000 main event.

Honourable Mentions

Vs Batista (Vengeance 2005, Hell in a Cell Match for WWE World Heavyweight Championship)

And Shawn Michaels vs Legacy (Summerslam 2009)

Vs Cactus Jack (No Way Out 2000, Hell in a Cell Match for WWF Championship)

Vs The Rock (Summerslam 1998, Ladder Match for the Intercontinental Championship)

Vs The Undertaker (WrestleMania XXVII)



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