Regardless of your opinion on the man and the performer, Triple H is undoubtedly one of the most decorated WWE superstars of all time. The current WWE World Heavyweight Champion has held a world title on 14 different occasions, and he has competed at 19 out of the last 20 WrestleManias, only missing out on WrestleMania 23 because of an injury.
With Triple H set to defend his title against Roman Reigns in one of the main events of WrestleMania 32 on April 3, it’s time to look back at each match The Game has had at the Show of Shows in his storied career.
#19. Hunter Hearst Helmsley vs. The Ultimate Warrior, WrestleMania XII
Triple H (under his original Hunter Hearst Helmsley gimmick) made his first WrestleMania appearance back in 1996 at WrestleMania XII where he took on the returning Ultimate Warrior in what was nothing other than a glorified squash match. Going back on it now, the only really interesting things about this 90-second match were Ultimate Warrior completely no-selling the Pedigree, which is much more jarring now than it was back in ’96, and Mrs. Brock Lesnar herself, Sable, making her debut as Triple H’s valet.
This match only existed to put Warrior over and is generally looked at like a stain on the early career of Triple H. He has said all of the right things about it, especially since Warrior’s passing in 2014, but yeah, nah, having one of your up and coming stars job out in a minute-and-a-half to a returner (who barely lasted three months in the WWF this time around) is dumb in any era.
#18. Triple H vs. Kane, WrestleMania XV
Raise your hand if you remember anything from this match besides Pete Rose dressing up as the San Diego Chicken? Didn’t think so.
This match is basically built all around Chyna, who turned on a babyface Triple H to join the corporation before the match. Surprise, surprise, though, Chyna switches allegiances again during this bout and rejoins her boyfriend at the time, Triple H, while Michael Cole attempts to sell this as the second-coming of Savage-Elizabeth.
Other than Triple H taking a crazy backdrop bump onto the floor and Kane diving over the top rope, there is really nothing here. It’s a bad match with typical attitude era booking, move along.
#17. WWE Championship Match: Triple H vs. Randy Orton, WrestleMania XXV
You could seriously make the argument that the decision to have the WWE Championship match main event WrestleMania XXV over a Shawn Michaels vs. The Undertaker matchup was one of the dumbest decisions ever made at a WrestleMania. If this match was somewhere else on the card, maybe it wouldn’t have been so bad. However, the crowd was absolutely emotionally spent after that match, and could not have been bothered to care about this match, which as a reminder WAS THE MAIN EVENT OF WRESTLEMANIA.
The build-up was all based on Randy Orton being a sexual predator because he was mad Evolution turned on him five years ago, or something, and right from the start things were just, well… boring.
After a stupid opening where they both hit finishers in the first minute of the match, there’s nothing here to justify their spot on the card. There’s a lot of kicks. And stomps. And headlocks. The stipulation added was that if Triple H gets DQ’d, he loses the championship (a stip they did a lot better two years later with Orton and Christian), but this match would have been improved tenfold if it was a street fight.
Instead, we got wonky ref bumps, allowing Triple H (the babyface, a reminder) to use the sledgehammer behind the official’s back and win. There’s a reason why this is regularly regarded as one of the worst WrestleMania main events ever. At the very least, WWE was smart enough to realize their mistake the next year and make sure that Michaels and Undertaker main-evented the show.
#16. Hunter Hearst Helmsley vs. Goldust, WrestleMania 13
Nineteen years later and both of these guys are going to be on the WrestleMania card, just take a quick second and appreciate that fact.
Anyways, Triple H was still trying to figure himself out in early 1997 when he feuded with Goldust, and this match is fun for that reason as you could see the later D-X character and Triple H’s move-set starting to develop.
Otherwise, there isn’t much to this other than to appreciate how much better in-ring Goldust is in the 2010s than he was in the ’90s, and a few nice ass-based moves on Goldy’s behalf that folks like Mojo Rawley and Naomi should take some notes on.
The finish gets messed up and is therefore far too reliant on Chyna not just WRECKING Terri Runnels (known as Marlena at this point) at the first opportunity she gets. If you’ve never seen it, here’s how I described it in my notes. It doesn’t make much more sense then I wrote it as, I promise.
Chyna walks over to Marlena while Goldust is going for the curtain call, but Goldy doesn’t see it. Hunter reverses and goes for the Pedigree, but now Goldust gets out of it and once again goes for the CC. NOW he sees Chyna, who at this point has been awkwardly staring at Marlena for like a minute. Hunter knees Goldust from behind with Marelna on the apron. Chyna catches her and bearhugs her and Triple H hits the Pedigree for the win. Sure.
You can probably skip this one.
#15 Triple H vs. Sheamus, WrestleMania XXVI
Despite the fact that he like just won the WWE title, it still never feels like Sheamus was as big of a thing as WWE was hoping for. This is evidenced by him getting a match with Triple H at WrestleMania in 2010, and no one at all remembering it.
This is all and all a solid, but forgettable match that gets dropped down a few spots because of the extremely questionable decision to have the Cerebral Assassin go over the still fresh-faced at the time Sheamus. The match itself is fine, with Sheamus doing his usual shtick and dominating most of the contest only for Triple H to hit a pedigree after two brogue kicks to win the match in around 13 minutes.
The best way for me to describe this match would be: “a pretty good SmackDown match,” so make of that what you will.
#14 WWE Championship Fatal 4-Way Elimination Match: Triple H vs. The Rock vs. Mick Foley vs. The Big Show, WrestleMania 2000
Oof, this match. Triple H and The Rock have had quite the rivalry over the years, and a singles match between the two would have probably ranked as one of the best of Triple H’s career at WrestleMania if that was the direction they had decided to go. Instead, we have a garbled mess that adds both Mick Foley and The Big Show and makes it an elimination match. Not to mention, as if just having the four of them out there wasn’t overcrowding it enough, each participant has a McMahon family member supporting them, because, The Attitude Era.
The Big Show is eliminated in like five minutes, and while Foley lasts a bit longer, he already had a great retirement match a month before this, and bringing him back here was so damn weird. Spin those two off into a singles and eliminate the McMahons from the equation, and you have a much stronger main event.
What we did end up getting was a sometimes brilliant, but too often frustrating match that really picked up in the last 10 minutes or so when it was down to Triple H and The Rock, but went off the rails again when Shane and Vince randomly start fighting and Vince turned on The Rock to have the heel walk out the champion.
There are some truly great spots and near falls in this, but there is way too much going on for it to be seriously recommended.
#13 WWE Championship Match: Triple H vs. John Cena, WrestleMania 22
Before we go into this one, I was not aware or did not remember that a certain Second City Saint made an appearance at this show as one of John Cena’s Chicago Mobsters or whatever, so that was a nice surprise.
Anyways, this match got over twice the amount of time as the Rey Mysterio-Kurt Angle-Randy Orton triple threat, which probably should have been the main event, but it was an okay, if not totally memorable main event.
Cena was also in full “get booed out of the building” mode, so it’s fascinating to see Triple H work heel when he’s getting cheers from more than half the crowd who just wants to see Cena lose in any way possible. Ten years later and he may be in the exact same situation with Roman Reigns.
The two have some good chemistry, but Cena was lacking the same in-ring quality that he brings to 2016 John Cena matches, and it feels like Triple H is just carrying him through most of it. It also didn’t help that the crowd had sabotaged the match by the end of it, cheering for Hunter when he got his sledgehammer after a convoluted ref bump.
The finishing sequence is pretty great, but it’s hard to get past Cena’s negative reaction and his limited in-ring skills at this point. There are worse WrestleMania main events, but neither one of these guys are including this in their “best of” DVDs.
Admittedly, this also might have been where my “watch an ungodly amount of Triple H matches in the same day” fatigue started to set in, so sorry if I’m selling it short.
#12. Triple H vs. Sting, WrestleMania 31
Basically, there seemed to be two different waves of thought regarding Triple H vs. Sting last year after it happened. Either you loved it and thought seeing everyone’s favorite ’90s wrestlers together again was great. Or you hated it and thought it was overbooked garbage to get more people on the show and were furious that Triple H actually won.
I felt closer to the latter opinion when I saw it the first time, but after going back now, I’m not as sure. Similar to Trips’ WrestleMania matches with The Undertaker (which we’ll get to later), this was less about the wrestling and more about the spectacle of it all. There were the insanely elaborate entrances. (Why would Sting even have a bunch of Asian percussionists? No one knows, but it’s kind of amazing.) The not one, not two, but THREE surprise run-ins. The bat breaking the sledgehammer in half. It’s all delightfully insane.
Still, though, there’s something that’s particularly sad about the fact that after everything, this was Sting’s first, and last WrestleMania match. He lost. He needed Hulk Hogan, Kevin Nash and Scott Hall’s help to fight off D-X. He had to shake Triple H’s hand and then put him over in promos for months and months when he feuded with Seth Rollins.
If they were able to have a rematch this year, maybe it all would have gone differently. Or maybe Sting could have given The Undertaker his second WrestleMania loss. But none of that is happening and this will in all likelihood be Sting’s only WrestleMania moment, and it ended with him taking half a sledgehammer to the face.
#11. World Heavyweight Championship Match: Triple H vs. Batista, WrestleMania 21
If there is any match that surprised me going back, it was this one. I feel like Triple H vs. Cena from 2006 gets more love on the internet, but I genuinely liked his battle with Batista from the year before more.
Big Dave was obviously still relatively limited at this time, but they found clever ways to work around it, and the crowd was super into Batista, which really helped. As usual, Ric Flair’s involvement makes everything better, as he tries multiple times to interfere and stop his former Evolution partner from winning the strap only to be put down.
The story of Batista winning the Royal Rumble and splitting from Evolution to go out on his own was well done, and Triple H putting the young guy over clean in the main event made it even better. This is one of The Game’s more underrated matches.
A Brief Aside About Triple H’s WrestleMania Entrances
Before we dive into the top ten, I would be remiss if I didn’t at least mention the pure insanity of Triple H’s many WrestleMania entrances over the years.
Other than maybe The Undertaker, there has been no WWE superstar who has had more bonkers WrestleMania entrances than Triple H. I could probably do an entire 5,000 words on his entrances alone. There’s just so much. From Sable, to Motorhead doing his entrance live twice and Lemmy not knowing the words either time, to shattering a glass mirror with a sledgehammer, to having Sasha Banks, Charlotte, and Alexa Bliss as his goddesses, to finally reaching his apex and literally entering the ring as a walking, breathing Terminator commercial.
I don’t know where he could possibly go from here, but I’m half expecting him to be carried to the ring on the Iron Throne this year.
#10. WWE Championship Match: Triple H vs. Chris Jericho, WrestleMania X8
Similarly to Triple H vs. Orton in 2009, his match with Chris Jericho at WrestleMania X8 is hurt by its place on the card. As great as Chris Jericho was and is, the crowd cared infinitely more about Hollywood Hogan and The Rock than they did about Y2J defending the undisputed title against a babyface Triple H. Because of that, the crowd is dead the entire match and no matter what either one of these guys did, it didn’t seem to help.
If you strip all that away, though, it’s still a pretty great wrestling match. Jericho spent most of it working over the leg because of Triple H’s quad injury, which also happens to make his leg-based submission finisher all the more dangerous. The match is moving along pretty well before Stephanie McMahon, dressed as an Austin Powers character, gets involved.
In an environment like Lucha Underground, watching a guy like Cage destroy Taya is okay because it’s being billed as a battle between relative equals. But watching Triple H pedigree his real life wife in the middle of a match to massive cheers evokes a bit of a different feeling.
Despite Stephanie’s involvement, the match really picks up towards the end, but the finish comes rather abruptly and it would have benefited from getting an additional 10 minutes. It’s disappointing, considering how good these two have been in matches with each other that their WrestleMania main event was just okay, but it wasn’t entirely their fault.
#9. World Heavyweight Championship Match: Triple H vs. Booker T, WrestleMania XIX
If Triple H vs. Booker T had a different result, it easily would be one of Hunter’s top five WrestleMania matches.
Unfortunately, when looking back on this match now, it’s tough to remember anything other than how furious (and rightfully so) everyone was that Booker T didn’t win. It’s straight up uncomfortable to watch Triple H call Booker a “common street thug” and hear Lawler on commentary make jokes like, “You know Booker T, whose family portrait is a courtroom sketch,” knowing how this all ends.
When people say things like “Triple H just buried everyone,” that’s not entirely accurate (his WrestleMania record is actually under .500), but it’s this match they’re talking about when they say it. At this point, there had never been a black world champion in WWE. This was the perfect time to do it, and they didn’t pull the trigger, and it made all the racist things they said in storyline about Booker all that much worse.
Having said that, the match itself is really, really, good.
Booker does something that no one outside of, like, Dolph Ziggler still does nowadays and actually sells the leg after it gets worked over because of interference by Flair on the outside. Booker really was straight fire here, hitting moves like the Harlem Hangover and just generally looking better than I ever remember him looking in WWE. If you pretend the last two minutes of this match went differently, it’s a pretty enjoyable watch.
#8. No Holds Barred Match: Triple H vs. Brock Lesnar, WrestleMania 29
By rule, anything is better if you add Brock Lesnar.
The result of this match was never really in question because Triple H had to “retire” if he lost, but Brock made sure that if he was going to lose at WrestleMania, he was going to beat the ever-living hell out of the COO first.
This was before Suplex City was a thing, but Brock does some of the most bonkers suplexes you’ll ever see in this match, including a belly-to-back through the announce table without even taking the covering off, and then another one straight onto the floor where the table used to be. He also does a hilarious screech thing after all of it. Brock Lesnar is amazing.
WWE was also starting to figure out at this time that if Lesnar was going to lose a match, you should have to literally throw the kitchen sink at him to beat him. Here, Brock survives a Pedigree, a Sweet Chin Music, three kimura locks, and a sledgehammer shot to the head before a Pedigree onto the steps finally puts him away. I would never book Brock Lesnar to ever lose, but at least they made him look like a million bucks before he took the three count.
#7. No Holds Barred Match: Triple H vs. The Undertaker, WrestleMania XXVII
The best way I can think of to describe this match is that it’s not a five-star match, but it is five-star theater.
On one hand, it’s pure nonsense. It’s all about making Triple H look like the biggest badass humanly possible without winning. There is legitimately nothing but finishers for the last 20 minutes of this. Undertaker kicks out of three Pedigrees and a Tombstone. I understand that it’s WrestleMania and the streak, but there is such a thing as too much, and this match comes extremely close to that line.
On the other hand, it’s objectively dramatic as all hell. Even though every single person in the building knew that Undertaker was not losing his streak to Triple H (although they all probably didn’t think he was losing it to Brock Lesnar either), the place goes bananas for the finisher kick-outs and Jim Ross is losing his damn mind on commentary. There’s no complex in-ring psychology or anything like that, it’s all about the drama of it all from the first second of the match to the last.
I didn’t absolutely love it. It’s not really for me personally and it’s not a match that I would choose to watch over again. But I can still appreciate it for what it is.
#6. European Championship Match: Triple H vs. Owen Hart, WrestleMania XIV
I was not necessarily expecting this mid-card match between Triple H and Owen Hart at WrestleMania XIV to be anything special going in, but thanks to the chemistry these two had together, it turned out to be a pleasant surprise and one of the better matches from the WrestleMania XIV card.
Owen had great fire as a babyface, and while it might not have been his most memorable match or anything, this is a good example to show those who weren’t around to see him how great he really was. Every little thing he does is crisp, clean, and smart. At one point, he hits a picture-perfect missile dropkick followed by a belly-to-belly suplex that is as great of a sequence as you’ll see.
Triple H isn’t a slouch either and holds his own with one of the best in-ring technicians of the era. It gets a solid amount of time and is way more fun than a lot of Triple H’s longer main event matches, and you should definitely check it out.
#5. WWE Championship Match: Triple H vs. John Cena vs. Randy Orton, WrestleMania XXIV
This match was everything that Triple H vs. Orton from a year later was not. Knowing that they only had around 15 minutes, all three of these guys worked at a brisk pace and crammed a lot of stuff into a 15-minute window.
There was some dumb stuff (like a rope break being called in a No DQ triple threat match), but for the most part, this was one of the better WWE triple threat matches you’ll see. They managed to avoid a lot of the “one guy lays around while two guys fight” thing that is so often used, and the finish of Orton coming out of nowhere to hit the punt on Triple H was genuinely surprising and well done.
I didn’t exactly have high hopes for this on paper, considering I feel like I’ve seen every combination of these three wrestle 700 times, but this was well done.
#4. Triple H vs. The Undertaker, WrestleMania X7
This match is pretty easy to overlook because it takes place on arguably the best WrestleMania card ever put together, but the first of the trio of WrestleMania matches between Triple H and The Undertaker was probably their best pure wrestling match of the bunch.
Although getting a match with The Undertaker is theoretically the second highest spot you can get on a card, you’d have to guess that Triple H was upset about his position because Stone Cold waltzed into the main event despite being out for much of the previous year. (Ironically, this all sounds relatively familiar to what happened in 2013 with one CM Punk.)
With something to prove, Trips had a very good match with The Undertaker that never really slowed down too much after a hot opening, even if fighting through the crowd and the convoluted set up to get on the soundboard or whatever was a little bit silly. I give them credit for making it work once they got there, though, with Triple H taking a pretty wild bump via a chokeslam onto the floor.
This match also features one of my favorite spots of all of these Triple H matches, when Hunter manages to grab the sledgehammer and hit Undertaker with it while he’s in position for the Last Ride, which I for sure bought as the finish at the time.
#3. Hell in a Cell Match: Triple H vs. The Undertaker w/ Special Referee Shawn Michaels, WrestleMania XVIII
I won’t say too much about this match because it’s similar to their prior effort a year before with a few noted improvements.
Although Shawn Michaels overdoes it sometimes (or, a lot of times) in this match, he undoubtedly adds an additional element that was missing from their match at 27. I think that the Sweet Chin Music into a Pedigree was probably one of the only times I thought for a split-second that the streak might actually end.
While I certainly don’t think it comes anywhere close to the level of The Undertaker-Michaels’ matches, I do think these hold up pretty well (despite the ridiculous insistence that this was “the end of an era.” Both of these guys are in main events four years later), if you take them for what they are.
#2. World Heavyweight Championship Match: Triple H vs. Chris Benoit vs. Shawn Michaels, WrestleMania XX
Basically, your enjoyment of this match boils down to how comfortable you are going back and watching Chris Benoit. If you’re able to separate the man from the performer, this is one of the best WrestleMania main events of all time.
Not only was Benoit beating both Triple H and Shawn Michaels at the same event one of the most compelling and unlikely stories ever told, the match itself is also five-star quality. There is some brilliant actual wrestling in the first half of the match (no surprise because Michaels and Benoit are two of the best in-ring performers ever), and the closing minutes are rife with incredibly tense nearfalls and submissions.
There’s one spot towards the end of the match where Michaels tries to tap out to the crossface, but Triple H stops his hand from hitting the mat. A few minutes later, Michaels superkicks Benoit as he has the sharpshooter on Triple H. It’s brilliant, and it all culminates with Benoit completing his unlikely journey by tapping out the most important guy on the show clean in the middle of the ring to win the world title and celebrating with Eddie Guerrero.
I know some people still can’t go back and watch Benoit’s stuff, and I totally get that. But if you’re able to remove the context and just watch it for what it was at the time, it’s an incredibly special match, and it’s a travesty that no one can ever talk about it.
#1. Triple H vs. Daniel Bryan, WrestleMania XXX
Two years later, and I still can’t believe this match really happened.
Daniel Bryan’s career didn’t exactly go as anyone was hoping for after WrestleMania XXX, but for that one night, the American Dragon was on top of the world.
Up until Bryan got the three count, people still believed that somehow Triple H was going to win and move into the main event, even though that would have made no sense in storyline. That’s how well this story was done. I’ve said it before, but whether or not Daniel Bryan beating the three biggest, baddest guys on the show in the same night to win the championship was always the plan (it wasn’t), WWE ended up telling one of the best and most complete stories in the history of wrestling with Daniel Bryan. It started with Triple H screwing him out of the championship at SummerSlam 2013, and ended with Bryan kneeing Triple H in the face and tapping out Batista at WrestleMania XXX.
Triple H deserves all of the credit in the world for being able to have this kind of a match at age 44 with one of the best workers in the world, and this was unlike any other of Triple H’s WrestleMania appearances. Hell, it might be the best match of his career.
It’s not just the fact that he put Bryan over clean as a sheet, but it’s that he was able to go move-for-move with the best wrestler in the world after being retired from full-time duty for four years. Say what you will about Triple H from 1998 to 2012 or whatever, but Authority Triple H is a damn legend, and this match proves it.
So, there you have it. Where will Triple H’s match with Roman Reigns rank on this list after next Sunday? Reigns has been sneaky good in-ring and exceeded all expectations with his match with Brock Lesnar a year ago, so don’t be shocked if it’s better than you think it will be.
Any of these matches you think I didn’t give enough love to? How about the ones I’m overrating? Let me know in the comments.
