10 Shocking WWE Stars Who Beat Triple H

Triple H has been a part of WWE for almost 30 years and he has morphed from a snobbish blueblood to a smutty degenerate to a jean-jacket-wearing badass to a big bald boss.

A legend in his own right, the former, Triple H had an in-ring career that ranks up there with the best and most dominant ever. He may be a skilled craftsman in the ring and have the look and the charisma necessary to make it to (and stay at) the top, but he also had one other thing help him out immeasurably.

No, we’re not talking about him settling down with the boss’s daughter because, let’s face it, that was a massive gamble that could’ve torpedoed his career faster than you can say ‘divorce’. We’re talking about favourable booking, particularly the fact that Triple H has won a lot more matches than he has lost, especially those on television and pay-per-view.

Yes, he’s took an L when going up against other megastars like The Rock, Undertaker, Shawn Michaels and Brock Lesnar, but he’s beaten just about everyone else there is to beat, leading to accusations of him holding down others to make himself look better.

That can quickly be debunked by exploring this rogues gallery list of wrestlers that Triple H has lost to, some of whom are truly astonishing.

These are 10 Shocking WWE Stars Who Beat Triple H.

10. Reverend D-Von

With the supposed ‘reign of terror’ just around the corner, Triple H did a rare job on SmackDown for Reverend D-Von, recently emancipated from partner Bubba Ray Dudley in the initial WWE draft.

The Game had not long lost the Undisputed Title to comeback king Hulk Hogan and was back to feuding with Chris Jericho, who he had beaten for the title at WrestleMania 18, but had lost to two weeks earlier on Smackdown.

Those tuning in to SmackDown on May 9, 2002 would’ve likely assumed that The Cerebral Assassin was going to handily destroy The Reverend, but that’s not how it shook out.

During the match, the preacher opened up a cut on Triple H’s forehead as the commentators repeatedly emphasised how he wasn’t at 100%. The former Dudley Boy also had a little help in the form of Deacon Batista, looking to impress in his debut and making himself useful by running interference at ringside.

In the end, it took an interfering Y2J to clock his foe over the head with the Rev’s collection box, leading to the unlikely result.

9. D-Lo Brown

A few years (and about 40 pounds of solid muscle) earlier, Triple H was more likely to be found fighting over WWE’s secondary championships than the main prize.

Even as the leader of D-Generation X Volume 2, Hunter wasn’t quite at the level to tangle with The Stone Colds and Undertakers of the world, but he did have a lengthy and fruitful feud with The Rock, also looking to break that glass ceiling, over the Intercontinental Title.

A key moment in that dispute came when Triple H defended the European Title against The Rock’s Nation of Domination pal D-Lo Brown on the July 20, 1998 episode of Raw.

D-Lo was no slouch, but he was still quite a bit further down the pecking order compared with the DX foreman. Their match was solid, as you would expect from two pros of their calibre. It did, however, veer off into shenanigans, as you would expect from a match of this era.

Chyna and The Rock, who were positioned at ringside, got involved before Mark Henry wandered out and provided the distraction, allowing The Great One to nail a Rock Bottom and hand Brown the title.

Four years later on Raw, Triple H beat D-Lo while blindfolded, so who really had the last laugh?

8. Jeff Hardy

In 2024, Jeff Hardy is a pro wrestling legend, a former WWE Champion who will go down in history as one of the most popular WWE superstars ever. Back in 2001, he was still popular but relatively unproven, especially at a main event level, as he had only really been tagging with brother Matt to that point.

When the Hardys engaged in a brief dispute with the Two-Man Power Trip of Steve Austin and Triple H, they (along with Lita) got their little arses handed to them, though the rainbow-haired warrior did get an Intercontinental Title shot against The Game out of it.

Colliding on the April 12, 2001 Smackdown, Jeff and Trips had themselves a canny little bout where Hardy stepped up his game (no pun intended), but the champ never looked in any real danger as he controlled the pace.

Frustrated with his inability to put the Charismatic Enigma away, The Game shoved down referee Tim White, giving Matt an opportunity to run in and blast him with a chair, which led to a Swanton Bomb and the shock title change.

Trips got the title back on the very next episode of Raw just days later, but it wouldn’t be the last time he did the honours for Jeff, putting him over again in 2007.

7. Shelton Benjamin

The 2004 Draft was a funny old thing. Triple H was sent to Smackdown but, in a desperate bid to get him back, Raw GM Eric Bischoff traded The Dudley Boys and Booker T.

Somewhat forgotten amongst all the bidding for The Game was Shelton Benjamin’s move to the red brand, splitting up the World’s Greatest Tag Team and forcing the excellent amateur practitioner to try his luck solo.

An immediate test was Benjamin’s first match on Raw, a main event against Triple H on March 29.

After a long, back-and-forth contest where Shelton emerged as a star, a ringside fracas between Ric Flair and Chris Benoit caught The Cerebral Assassin’s attention long enough for Benjamin to nail a Stinger Splash and roll him up for the three.

Playing off the improbable win, Shelton got a count-out victory over Triple H the next week, a disqualification win a few months later, and took him to the absolute limit in a Beat the Clock Challenge match on the last Raw of the year.

2004 was a breakout year for the Gold Standard and his series of matches with Triple H had a lot to do with legitimising him in the eyes of the fans.

6. The Stalker

As a mark for vintage NWA from the 70s and 80s, I doubt a still-developing Hunter Hearst Helmsley would’ve minded putting over Barry Windham.

Windham, one of the most underrated workers ever, who never quite fulfilled his enormous potential, was a former NWA Worlds Heavyweight Champion and Four Horseman member.

Triple might have had an issue doing the honours for The Stalker, however. The Stalker was Windham repackaged as some sort of camo-wearing, face-painted hunter, a gimmick given to him because he happened to mention he liked outdoor pursuits during an interview with Vince McMahon.

The Stalker came out strong, getting a decent little push in late 96, beating the likes of The Goon and TL Hopper. His biggest scalp was Helmsley’s, beating him with a Superplex on the September 23 Raw.

Hunter was, perhaps, still serving some of his punishment for his part in the infamous MSG Curtain Call as, before that night, he was far better protected on television.

5. Curtis Axel

The son of the late, great Mr. Perfect was earmarked for superstardom by WWE higher-ups but his career initially stuttered due to his torrid time on NXT, rubbish ring name and forgettable run as a member of Nexus.

Re-debuting under the new name of Curtis Axel and paired up with Paul Heyman as his manager in the Spring of 2013, his career received a big boost as he said goodbye to the minor leagues and set his sights on climbing the ladder on Raw.

Paul Levesque, as an influential force in talent relations, saw great things in Axel’s future and predicted he could be one of the men to carry the company in years to come.

History has shown that it didn’t quite work out that way, but Trips did his part to elevate the upstart regardless.

First, The Game lost to Axel via knockout when he received a storyline concussion during a match on the May 20 Raw, which was Axel’s first match back after another spell in developmental.

Then a few weeks and a few more wins later, Axel beat Triple H not once but twice on the June 10 Raw, first by disqualification and then by forfeit, though it was admittedly more of an angle than a real match.

Axel never pinned his opponent or made him submit, but the three victories, however he got them, gave him some bragging rights nonetheless.

4. Test

Another wrestler who holds multiple victories over our man is Test.

It was earlier in the evening of the infamous wedding episode, before the hijacked ceremony went down, that Test got his first victory over Triple H.

Test was given a match with the King of Kings as a wedding present from Vince McMahon.

Stacking the deck against Triple H was the fact that someone in a truly chilling Vince McMahon mask was refereeing the contest, his dodgy officiating causing The Game to go after him, giving an opening to Shane McMahon to run in with the chair, setting up the big elbow from the groom-to-be, with a quick count thrown in for good measure.

A couple of years later and with the ruined wedding a distant memory, Test (then a member of the Un-Americans) got another win over Triple H on the May 30, 2002 edition of Smackdown, securing the pin thanks to interference from both Lance Storm and The Undertaker.

3. Jim Ross

Embarrassing Jim Ross was a favourite pastime of Vince McMahon, one that his son-in-law clearly inherited, if his match with Good Ol’ JR on the April 18, 2005 episode of Raw was anything to go by.

And this was no ordinary match. This was a No Disqualification main event in Madison Square Garden. The Game pounded the announcer for what seemed like an eternity, busting him open with a potato shot that was very out of character by a performer who was usually such a safe pair of hands.

Jerry Lawler, either concerned for his pal or as bored by the alleged contest as the rest of MSG, tried to intervene on JR’s behalf but promptly got his crown kicked in.

Eventually Batista, who was supposed to be in the Oklahoman’s corner but sauntered into the arena in a limo about three minutes before the show went off the air, evened things up with a steel chair, draping a half-dead JR on top of his former mentor for the win.

2. The Godfather

One of the great things about the Attitude Era was that seemingly every character, no matter how minor, had something going on.

From the main event to the opening match, everyone on the card had an angle or a storyline or something happening for them and it worked wonders for performers like The Godfather.

He may not have been challenging for the WWE Title, but he could still realistically fight the WWE Champion, which he did when he met Triple H on the March 16, 2000 episode of SmackDown.

A couple of weeks before The Game was due to defend the belt against The Rock, Mick Foley and Big Show at WrestleMania, he went up against the conductor of the Ho Train in what really should have been a routine win.

Interference from Show and his cornerman Shane McMahon saw the short match go in favour of the Pimp Daddy, although Trips did kick out on 3.1, so it looked like he didn’t really lose.

1. Brooklyn Brawler

So far we’ve seen Triple H looking at the lights for legends, promising upstarts and even a commentator, but of all the wrestlers to score a W over the Cerebral Assassin, the Brooklyn Brawler is probably the most shocking.

The veteran was basically a career enhancement talent, getting paid to do the honours for everyone else on a nightly basis and, by the time he met Triple H on the July 6, 2000 episode of SmackDown, he was older and had transitioned into a backstage role with the company.

The New York Native was put back in the ring to help further the storyline between Triple H and Chris Jericho.

Trips had to beat Brawler and Kai En Tai in an elimination handicap match in order to get a crack at Y2J a few days later on Raw.

While Triple H had little issue disposing of Funaki and TAKA Michinoku, timely interference from Jericho gave the Brooklyn Brawler a memorable victory.