25 years of Triple H in the WWE…how time flies! A few days ago, I put together a list of HHH’s Top 10 Greatest Matches. I’m all in favour of yin/yang, light/dark, good/bad, so it would be remiss of me not to do a list of his worst matches! HHH has been involved in some dire matches. Just look at his WrestleMania main event record; he’s wrestled in the main event seven times…but at least four of those were incredibly boring. In fact, I can only name one time HHH has really pulled out all the stops in a ‘Mania main event: WrestleMania XX.

HHH is also notorious for refusing to put other wrestlers over, “burying” other wrestlers, wrestling through injuries, and returning from injuries only to “bury” other wrestlers. All of these elements have resulted in awful matches. To make it fair, I’ve tried to stay away from HHH’s ‘Mania matches that have stunk up the joint. So you won’t see his main events against Chris Jericho, Roman Reigns, or the infamous WrestleMania 2000 Fatal 4-Way main event here. I’ve looked over some of his more unknown stinkers as well!

(Click here for Hammy’s Top 10 Greatest HHH Matches!)

hhh wrestlemania entrance
HHH may have some great WrestleMania entrances…but they usually lead to awful matches!

So, without further ado, here are HHH’s Top 10 Worst Matches…

  1. vs Shawn Michaels (Armageddon 2002, 3 Stages of Hell Match for WWE World Heavyweight Championship)

I think HHH’s most famous 3 Stages of Hell match, against Stone Cold, is overrated. Yes, it’s good, but it’s too drawn out and becomes a slog to watch in its third act. This one, pitting HHH against HBK, however, is awful. Yes, you heard correctly: a poor HBK match! The problem was that HHH was wrestling with an injury. HBK tries his best, but HHH is slow and sluggish here….and the match goes on and on. The first pinfall in a regular wrestling match is boring. The second, a No DQ match, fares little better, as HHH struggles to keep up with HBK. The third, a cage match, simply potters on, with HBK trying in vain to spice up the match until it stutters to an end. Maybe I’m overly harsh on this match…but at the time, I was incredibly excited for it. Their feud, stretching back to Summerslam 2002, had reached boiling point. This would be a fitting end. Instead, they dropped to absolute zero. A crying shame.

  1. vs The Great Khali (Summerslam 2008, WWE Championship Match)

Could anyone drag a decent match out of The Great Khali? I doubt even Flair in his prime could. On the night of Summerslam 2008, it fell to Triple H to try to drag Khali to a decent match. And….Triple HHH failed. As chants of ‘you can’t wrestle’ hounded Khali throughout the match, Khali put weak-looking hold after weak-looking hold on HHH in a poor attempt to build heat. It didn’t work. HHH was always better as the heel, building up his opponents for a comeback. Here, HHH;s comebacks don’t land as well as they do, probably due to the Khali’s inability to sell, and HHH’s lack of experience as a babyface. Not the worst match in Summerslam history, but one of the dullest. It also makes me wonder…why were the WWE so intent on getting Khali over? It baffles me to this day.

  1. vs Booker T (Summerslam 2007)

Poor Booker T…HHH would never give him a break! At WrestleMania XIX, HHH waited what seemed like an hour after hitting T with the pedigree to pin him and end the bout. Why? To embarrass Booker T? Their prior storyline, centred around racism, was a vehicle for Booker T to be triumphant. Instead, HHH beat him definitively. At least the twenty minutes before that Pedigree were half-decent. Here, in HHH’s return match from yet another quad injury, the result was not in doubt. HHH was going to win. But would he let Booker T look like a winner in defeat? In short, no. It took HHH 8 minutes to defeat Booker T, eight minutes that made it clear HHH had returned too soon. He was slow, tentative, and unwilling to sell properly. I’d be scared of tearing my quad yet again if I was HHH, but that doesn’t excuse his performance. Booker T phoned in his performance as well (I don’t blame him). A truly dire bout.

  1. vs Goldberg (Unforgiven 2003, World Heavyweight Championship Match)

Goldberg was never a wrestler to go longer than ten minutes. There’s nothing inherently wrong with that, but all WWE seemed to want him to do during his first tenure with the company is wrestle long matches (well, long for Goldberg). His first bout against The Rock went on far beyond Goldberg’s comfort zone. Midway through his debut year, WWE wasted the perfect opportunity to put the World Heavyweight title on Goldberg in the Elimination Chamber match at Summerslam 2003. Instead, he had to wait until defeating HHH in a long, drawn-out waste of a match. Yes, HHH is always effective as a heel, but here he seemed reluctant to properly sell for Goldberg. It should have been a short, sweet squash match. But no. HHH, still possibly suffering from an injured groin, wanted to put on a “wrestling” match with Goldberg. The result: HHH dominating much of the match, only occasionally allowing Goldberg to hit a big move. Boring, unnecessary, and a waste of Goldberg’s talents. And a few months later Goldberg would lose the title back to HHH!

  1. vs Randy Orton (WrestleMania 25, WWE Championship Match)

WM25 is only remembered for the sublime collision between HBK and The Undertaker. That wasn’t the main event, however…Triple H, yet again, was in the main event, against frequent opponent Randy Orton. Their feud is full of matches ranging from poor to great. This…this is poor. After a lengthy build that featured Randy Orton assaulting and then kissing Stephanie McMahon (in front of a handcuffed HHH, no less) and a home invasion by HHH, this needed to be a full-on, violent brawl. Instead, it was a pedestrian bout that went on for far too long. It lacked much of anything. No pacing, no story…just a bout that made you want to go to sleep. The WM main event should be the crème de la crème of the card…and this was the sour, spoiled, cream left on the windowsill for days. Of course, this wasn’t the first example of HHH stinking up the ‘Mania main event…and it wouldn’t be the last.

  1. vs Henry Godwin (In Your House 5, Hog Pen Match)

Did you ever want to see HHH flop around in pig excrement? If your answer is ‘yes,’ then this bout is for your and other coprophiliacs! This was part of HHH’s punishment for being involved in the famous ‘Curtain Call,’ where ‘The Clique’ broke kayfabe at Madison Square Garden. And while HBK continued on as WWF Champion, HHH was reduced to wrestling in crap…against the crap Henry Godwin. There’s nothing redeemable about this bout whatsoever. To win the bout, you have to throw your opponent inside the pig pen. Henry Godwin was an awful wrestler, and presumably HHH didn’t care, so they go through the motions is the dullest manner possible until HHH is thrown into the pig crap. A perfect metaphor for the match itself.

  1. vs Ultimate Warrior (WrestleMania 12)

The Ultimate Warrior made his second return to the WWE at WrestleMania 12, and to put him over immediately, WWE chose HHH to lose to him in a squash match. Now, there’s nothing inherently wrong with squash matches. Done right, they can put over a wrestler’s ferocity/strength while being a short but sweet bit of entertainment. That’s all Warrior was famous for, if you think about it (I’d wager he had less than five decent bouts in his entire career). But here, he didn’t show any pizzazz, anything of value as he quickly put HHH away in 92 seconds. Yes, on the grandest stage of them all, HHH lost in 92 seconds (in his WrestleMania debut, no less!). It was over before you could eat that hot dog you just made. It made no impact, and Warrior left not long after. All in all, a pointless squash match.

  1. vs Jim Ross (WWE Raw, 18/5/2005)

Jim Ross in the main event of a Raw? Yes, and it’s as bad as it sounds. Vince McMahon always loved to embarrass good ol’ JR, and this bout is typical of McMahon’s treatment of the beloved commentator. Why even put him in the bout, and a No DQ bout to boot? It didn’t make sense! What ensued was a plodding slog as HHH pummelled JR into oblivion (for real, at one point; JR’s face was clearly bruised halfway through the match). Even if they’d put Jerry Lawler int eh bout instead of JR, that would have made more sense. JR couldn’t sell. JR didn’t know anything about in-ring psychology. In the words of JR himself, it quickly turned ‘bowling shoe ugly,’ descending into farce. What tops off the farcical nature of the bout is that JR wins! With the help of Batista…but think about it! HHH wouldn’t put over RVD, Booker T, Chris Jericho… but he allowed JR to have a pinfall victory over him!!!

  1. and Shawn Michaels vs The Undertaker and Kane (Crown Jewel 2018)

What could go wrong, putting four men in a match with a combined age of nearly 200? What could go wrong, ruining HBK’s retirement for a massive single payday that lacked any efficient build or excitement? What could go wrong, seeming as The Undertaker could barely walk? Well, everything. All wrestlers looked exhausted by the ten minutes mark…and then HHH injured himself, tearing his pectoral muscle. Valiantly, he carried on, but it fell to HBK to carry the rest of the bout. HBK in his prime couldn’t carry the weights of old Taker and old Kane, and he fails here, almost killing himself with a moonsault of the top rope to the outside. An absolute shambles of a match that exemplifies everything that’s wrong with WWE’s Saudi Arabia shows. Of course, I’m most annoyed that they ruined HBK’s retirement for a pathetic payoff…but regardless of my feelings about that, this is one of the worst WWE bouts of the modern era.

  1. vs Scott Steiner (Royal Rumble 2003, World Heavyweight Championship Match)

hhh scott steiner royal rumble

Scott Steiner came to the WWE in late 2002 with a fantastic pop. The crowd were excited to see ‘Big Poppa Pump’ return to the WWE. Wisely, WWE kept him away from the ring…and then shoved him into the World Heavyweight Championship picture against super-heel HHH. They were scheduled to clash at Royal Rumble 2003…and what ensued was one of the worst bouts in Rumble history. Steiner was full of injuries, and HHH still wasn’t back to his pre-quad tear form. Botches, missed spots, slow pacing, no-selling, miscommunication…nothing went right in this bout. It was clear Steiner was in no condition to wrestle, and the crowd’s excitement to see him soon descended into a shower of boos. It didn’t help that the following bout, Angle v Benoit, turned out to be one of the best bouts in WWE history. But even compared to Dawn Marie Wilson v Torrie Wilson, HHH v Steiner was awful. A contender for the worst bout in WWE history.

Honourable Mentions

Vs Chris Jericho (WrestleMania X-8)

Vs Roman Reigns (Wrestlemania 32)

Vs Scott Steiner (No Way Out 2003)

Vs CM Punk (Night of Champions 2011)

Vs Kurt Angle (Unforgiven 2000)

Vs Kevin Nash (Ladder Match, TLC 2011)

Vs Vladimir Kozlov vs Edge (Survivor Series 2008)

Vs Sting (WrestleMania 31)


  1. Chris McCarthy May 6, 2020 / 4:46 pm

    Fun and informative article. 👍

    Liked by 1 person

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