The Most Surprising Losses Of Triple H's Career

Pre-Curtain Call, Helmsley was well on his way to becoming a big-time heel in the WWF and giving him the responsibility of working with a returning Ultimate Warrior at WrestleMania tells you enough about the favor he was in at the time. Having been away for four years, Warrior's return was a big deal with a ton of fanfare. So a loss here for Helmsley wasn't as surprising from a result perspective as it was the manner in which it went down.

Helmsley enters with a debuting Sable as McMahon, on commentary, quickly begins to tee up the scenario at hand. What kind of shape is Warrior in? Can Helmsley execute the Pedigree on a man of his stature? Warrior's physical appearance was never to be questioned, but from a stamina perspective what was about to happen was probably the best he could do at this point. Following the trademark Warrior entrance to hype the crowd, Helmsley attacks before the bell, shockingly hitting a Pedigree on Warrior, not yet out of his entrance jacket, but the budding trademark finisher is completely no-sold. From there, it's a Warrior match on fast forward. Warrior delivers one punch, three straight clotheslines, a shoulder tackle, the gorilla press, the splash, and we get a 1-2-3. The match was 1:39 from bell to bell.

"I'm not too sure that Hunter Hearst Helmsley knew what hit him," McMahon would utter. In the moment, the loss seemed like a momentum killer, but Helmsley got back on track with a win over Duke "The Dumpster" Droese on "Raw" and knocked off Marc Mero (who had acquired the services of Sable) at In Your House 7 just a few weeks before a public goodbye to Diesel and Razor Ramon would take care of that whole derailing thing after all.

Ah, it's the dawn of the McMahon-Helmsley era in full effect. The surprise in this match is that Triple H had absolutely everything going in his favor with not just Stephanie, which was common practice by this point, but also Vince in his corner, and Shane as the guest referee. Even Linda, upholding whatever valor might be left in the McMahon name at the time as the contrarian to the evil of the others, trying to even the odds by putting "Stone Cold" Steve Austin in The Rock's corner was seemingly thwarted when Vince announced that Austin would not be appearing after all, just as the match was set to begin.

With the cards stacked against The Rock, it was clear that it would take all sorts of hoopla for Triple H not to win, and all sorts of hoopla is exactly what we got. The Rock was a force at this point, so the fact that he battled through was no shock to anyone — and a double Rock Bottom on HHH and Shane through the Spanish announce table was a pretty damn cool spot that seemed to turn the tides. Eventually, though, Vince hits the ring for a low blow, HHH hits a Pedigree, and Pat Patterson and Gerald Brisco come out with referee shirts on, only to join in on the beatdown after an unsuccessful three count. After Vince blasts The Rock with a chair, finally, Austin makes his way to the ring with chair shots for all, including a pair for Hunter before he heads backstage. Linda joins the fray with Earl Hebner in tow, shoving Steph down, and then Rock hits a spinebuster and The People's Elbow. From there, it's an oddly slow 1-2-3 from Hebner and all odds are defied and The Rock is your new WWF Champion.

This one won't ever be remembered as a wrestling classic as one might quickly surmise about a Goldberg match that went nearly 15 minutes, but it makes the list nonetheless thanks to the result. The feud began when "The Game" retained his title in the Elimination Chamber at SummerSlam thanks to his trademark sledgehammer and some help from Evolution. The next night on "Raw," Goldberg sought revenge and demanded a title shot, which HHH granted under one condition: A Goldberg loss would mean he'd have to leave the company. That was surely not happening at this point in Goldberg's career, which maybe takes away from the surprise element a bit, but we're sticking with it as him going over Triple H in a World Title match in WWE is certainly something most never thought they'd see.

The additional stipulation of champion's advantage not being in play, as a disqualification or count-out finish would also see HHH lose his title, effectively eliminated any chance of interference from his Evolution counterparts. Still, "The Game" was able to get away with a sledgehammer shot after a ref bump, but it was largely no-sold by Goldberg who hit a spear to turn the tide right after. After following that up with a jackhammer, that was it. Goldberg grabbed WWE gold for the first time in his career and Hunter would have to settle for a rematch at Survivor Series. Unsuccessful there as well, he'd finally overcome Goldberg at Armageddon, with a little assistance from Kane, who had been thrown into the mix since the previous singles matches in this feud were met with little fanfare.

The best thing to come out of all of this was a rekindling of the HHH and Shawn Michaels rivalry, culminating in an epic three-way at WrestleMania XX, which just so happens to be next on our list.

The 2004 WWE Draft broke up The World's Greatest Tag Team and shifted Shelton Benjamin over to "Raw," where he'd make his in-ring television debut in a main event showing against Triple H. While Benjamin would go on to three straight victories over "The Game," launching him into high profile storylines against fellow Evolution members Ric Flair and Randy Orton, it was their first encounter — the only win by pinfall of the three — that stands out as a shock to this day.

Triple H had actually been drafted to "SmackDown," seemingly breaking up Evolution, but was traded back to "Raw" almost immediately, reuniting the faction and setting up this showdown with Benjamin. Of course, this meant a backstage beatdown from HHH's cronies, further diminishing the chances for Benjamin in their match later that night. The showdown was hyped up to be a big deal throughout the show, with Benjamin getting encouragement from the likes of Mick Foley and then-World Heavyweight Champion Chris Benoit, with the champ factoring into the decision by thwarting a Flair interference attempt. By and large, however, HHH put the shine on the up-and-coming Benjamin, stunning the crowd and earning this match its place in history (or at least on this list).

While it may not have elevated Benjamin into the stratosphere as a singles star as might have been intended, it certainly boosted his credibility, which has sustained itself all these years later as Benjamin is regarded as one of the most underrated performers in WWE history.

With both Triple H and John Cena battling back from major injuries, plus a heel Randy Orton as the defending champion, the prevailing thought heading into this Triple Threat was that one of the babyfaces would come away with the title. But that was not to be. Cena earned his way into this match following a Royal Rumble win in his surprise return from a torn pec muscle (though initially, he used his title shot at No Way Out and won by disqualification, ultimately setting up this pseudo-rematch), while HHH punched his ticket by winning in the Elimination Chamber. Pair all that with the fact that Cena got the royal entrance treatment, complete with a marching band, and HHH's entrance being, well, a Triple H WrestleMania entrance, and you might have placed a large wager on Orton not coming away as the victor. (Note: If you gamble on pro wrestling matches, you might have a problem.)

With each man hitting his trademark moves throughout the contest, this was truly a back and forth (and back again) battle. Triple H strayed from his usual bag of tricks at one point, slapping an Indian Death Lock on Orton before Cena broke that up as the match raced toward its crescendo. The end result came after false finishes for both faces including the finale, a Pedigree on Cena that went for naught when Orton hit not an RKO, but a punt out of nowhere and got the pinfall to retain.

While the outcome was a bit surprising on account of the successful returns from injury for both Cena and HHH, the latter would go on to win back his championship in a return engagement with these two (plus JBL added to the mix to make it a fatal four-way), by pinning Orton at Backlash.

That's right, Curtis Axel defeated Triple H. He defeated him twice, in fact! Axel, recently repackaged from his days as Michael McGillicutty, was re-debuting as "a Paul Heyman guy" and seemingly was set for a big push. Just having a match against a future Hall of Famer on his first night under the new gimmick would certainly double down on as much.

HHH was coming off the third match in his trilogy against fellow part-timer Brock Lesnar the night before in a steel cage at Extreme Rules; it was a loss from which he'd still be selling the damage here a day later. That, one would think, would have been the tell. A win over a severely compromised anyone wouldn't do much for Axel, and the performance by Triple H showing signs of being supposedly concussed by Lesnar was pretty over the top. The finish was rather forgettable, with a disoriented HHH trying to get his bearings outside the ring, pouring water on his head and flopping like a fish while trying to get back into the action. As trainers advised him to shut it down, the referee counted him out and Axel was named the winner.

This prompted an angle for the pseudo-retired Triple H, with family trying to get him to stop competing altogether. Eventually, Axel would beat him again when Vince McMahon called a stop to their return engagement. The pair of wins over "The Game" didn't do a lot for Axel, whose pedigree as the son of Mr. Perfect and grandson of Larry "The Axe" Hennig was understated throughout a career highlighted by an underwhelming Intercontinental Championship run and time spent as one half of The B-Team alongside Bo Dallas. From here, Triple H would go on to establish The Authority, never to speak of the ramifications from that concussion ever again.