Alex has been an online sports and pop culture writer for five years. When he's not writing about sports, Alex is an aspiring screenwriter.
Triple H is a man with a complicated legacy. His detractors point to him as someone who has hogged championships, abused his political power, and buried talented workers either as a worker with his reign of terror or as an on-screen authority figure with his wife. However, he is also a talented worker who was known for being a ring general and a savvy booker. (His brilliant booking for NXT feels even more pronounced after Vince usurped the job and wrecked the show.) He’s also proven to be a legit tough guy, having seen matches to the end even after suffering severe injuries. With his recent retirement falling so close to Wrestlemania season, it’s time to look at some of those highs and lows. This ranking will be from worst to best.
Vs. Kane (WrestleMania 15)
I remember in the build for Wrestlemania 24, Raw held a special “Wrestlemania Rematches” Night. The roster didn’t actually have enough people to live up to that lofty promise, so mostly they had to use money in the bank participants and retread matches like this. It was pretty funny hearing the commentators talk about this mid-level match like it was something anyone cared about. One reason I bring that up is that there’s not much to talk about with this one. It was a Raw level match that ended in disqualification. The DQ was the result of Chyna interfering to help Triple H. That may sound like a feel-good moment, but it was quickly nullified by both of them turning heel later that night. Honestly, the most entertaining part of this match was Kane’s continuing feud with Pete Rose.
Vs. Randy Orton (WrestleMania 25)
There was one challenge in ranking a lot of these matches. Triple H has had some rubbish matches at Mania but fewer major stinkers than one might think. Most of his bad matches are just pedestrian. The crime is that they were mediocre matches in a situation where fans expected something special. So, the worst on this list may not be the absolute worst thing ever, but this is a ranking of one man’s matches.
I distinctly remember people calling it the worst main event in Mania history. There are certainly worse, but this match’s reputation as a stinker is well-earned. First of all, this match was already in a no-win scenario (Not the last time I’ll be saying that). It had to follow the epic Shawn Michaels-Undertaker match and a triple threat between Cena, Edge and Big Show (one of the most underrated title matches in Mania history). Despite being built up as a blood feud, Orton and the H-man had a match so blasé, fans would demand better if it were the main event of Backlash. The decision to add the stipulation that if Hunter got disqualified he’d lose the title was baffling, as a no-DQ match might have gotten this into that next gear.
Vs. Roman Reigns (WrestleMania 32)
Ah, the favorite Wrestlemania match of no one. What was supposed to be the big coronation of Roman Reigns was instead such a disaster, fans didn’t warm up to the guy until his 2020 heel turn. Triple H absconding with the title at the Rumble months prior reeked of the bad old days. To Hunter’s credit, he had a good match as champion. Too bad it was at a souped-up house show against the much more over Dean Ambrose. Reigns was working on getting better, but the length also exposed his weaknesses. This match wasn’t the worst thing ever, but a so-so match, McMahon hubris and a champion nobody really wanted at the time were all a perfect storm of a middling main event.
Vs. Batista (WrestleMania 35)
More and more, this match is beginning to feel bizarre. Batista has been in both Hollywood blockbusters and a Best Picture nominee but decided to have one final hurrah in the business that made him a star. Pretty much everyone had a joke about how the guy who typically had less than 3 matches a year was putting his career on the line, especially since WWE did this song and dance before. The match itself was a little clunky. Unlike the last two lousy matches, this match went for a hardcore brawl – definitely playing to both men’s strengths. But it was still too slow-paced for its own good. The most memorable spot was when Triple H straight-up pulled out Batista’s nose ring. That spot made me wince when I saw it, and I winced again watching it for this article. It’s debatable if this match is actually worse than the previous two, but this stayed in its lane and at least had one memorable visual. Also, Triple H had maybe 2 televised matches after this. So, Batista got what he wanted!
Vs. Ultimate Warrior (WrestleMania 12)
This will not be the first time someone points out the irony that someone who made a career out of burying people (and now practically owns the company) made his Wrestlemania debut getting squashed by Warrior. Also, it’s proof that WWE feeding their young talent to the stars of the past isn’t new. But the positive of this being a squash is they knew to hide Warrior’s limits. It’s not hard to picture this match happening now and trying to get a 15-minute match out of it (shiver). And for better or worse, the crowd WAS into it. Even if you’re not a hardcore Triple H-hater, this match is only interesting as a curious piece of wrestling history.
Vs. Sting (WrestleMania 31)
Sting – the one man who eluded working for the WWE for over a decade. The man was finally under the WWE umbrella and finally made his Wrestlemania debut. And sure enough, he jobbed to Triple H because Vince wanted one last nail in the coffin of WCW. It was tempting to rank this match lower but at the same time… It isn’t NOT entertaining. Still, the DX vs. NWO stuff made zero sense, and Sting looked like a chump for making a big debut at Survivor Series only to job out. Plus, Hunter shilled for a mediocre Terminator movie that if anyone remembers it, they’d probably rather not. This is the one match that actually borders on so bad it’s good.
Vs. Brock Lesnar (WrestleMania 29)
Boy, WWE sure loves going to the well of threatening Triple H’s in-ring retirement when everyone knew he was a part-timer. By this point, Lesnar only had two matches since his return the previous year. One of them was a submission win over Triple H, so wanted or not – this at least made sense. The match is relatively clunky – nothing egregiously wrong. And there are SOME entertaining spots. But in broad sweeps, this match felt like it just ambled from Lesnar whooping Triple H and waiting for Hunter to make his big comeback. Once again, Triple H’s belief that long matches equal good matches led to this being about twice as long as it should have been. Also, Shawn Michaels was there to take some hits. Amazingly, the two had a MUCH better match at Extreme Rules when they were confined to a steel cage.
Vs. Goldust (WrestleMania 13)
I feel like I could rattle off most of the matches on this list from memory, but I had to look up what match happened at Wrestlemania 13. Shame, because this is kind of underrated. Mania 13 is considered a one-match show. But maybe, it’s a THREE match show. Okay, Triple H and Goldust did nothing mind-blowing, but they did put on a serviceable IC title match. So maybe next time you feel like watching the epic Hart-Austin “I Quit” match, check this one out too (And the Chicago street fight).
Vs. Chris Jericho (WrestleMania 18)
Yet another match where The Game was more or less in a losing situation. The Rock vs. Hogan was the real star, and maybe it would have been prudent to make that the main event. Unlike, the aforementioned Orton match, this was not built as a blood feud. No, this was a POOP feud. And there was spousal abuse. This is probably why there was no video package. This match at least felt like a PPV main event, it just never hit that next gear a Wrestlemania main event needs.
Vs. Owen Hart (WrestleMania 14)
A recurring theme on this list has been that Triple H’s mid-match bouts have outranked his big main event matches. Simply put, those matches lived up to their own standards. Owen Hart was a gifted worker so it makes sense that he and Triple H had good matches. The story of Chyna overcoming her handcuffing to Sgt. Slaughter in order to help Triple H win was entertaining and helped sell them as heels. My one knock against this match is that it continued the downward slide of Owen’s character from tough guy to chump. (He even showed some of that bravado at the beginning.) But DX was growing in popularity and soon had a big face turn. Maybe the company made the right call.
Vs. Sheamus (WrestleMania 26)
This match felt like a changing of the guard. After inserting himself into some kind of main event or title match of Wrestlemania for nearly a decade, this was the first time in a while Triple H was involved in a simple mid-card match. It was also the last time The Game fought as an active wrestler and not an annual attraction. Triple H won a solid match, which was okay because Sheamus earned his mojo back in a big way, even winning the WWE Championship later that summer.
Vs. The Rock Vs. Mick Foley Vs. The Big Show (WrestleMania 2000)
Was this match overbooked? Oh yeah? Was it entertaining? Somehow. This was the first time the main event of Wrestlemania was more than a one-on-one showdown. It’s also easy to see why this was the last time they tried a four-way. Four way elimination matches just don’t lend themselves to the drama that a one-on-one or triple threat match can. It’s a bit of a devil’s bargain: rarely bad but rarely exceptional. And while it was a novel concept, fans were not as interested in every wrestler representing a McMahon. At the same time, the match is mostly entertaining. There’s hardly a dull moment, and there is some psychology as the four men form unlikely alliances. Though there was an uncomfortable spot when Mick Foley whiffed his elbow dive. This was also noteworthy as the first time a heel won in the main event… without Hulk Hogan there to “save the day.” I mean, who wants babyface Vince McMahon?
Vs. John Cena vs. Randy Orton (Wrestlemania 24)
Maybe there’s another reason Orton/HHH didn’t get over at 25. Fans already saw a similar match a year prior. But since Cena was removed from the equation, it LOWERED the ante. There was nothing terribly wrong with this match, and there was a much better world title match later that night. But with three talented workers, they kept the flow going and never let it get dull. Though heel Orton winning out of nowhere did suck the life out just a little. But overall solid match.
Vs. Seth Rollins (WrestleMania 35)
Not going to lie, I thought Triple H riding around the ring on the motorbike was kind of cool. Despite Rollins and Triple H making sense on paper, but Rollins hadn’t quite gelled as a face and it took a while after the opening salvo for Hunter to even return to TV. This is another one to file under good but not great. In matches with Dean Ambrose and Daniel Bryan, Triple H proved he could still go in no-frills matches, but this was a no disqualification match – a no-DQ match that barely took advantage of the rules.
Triple H working Rollins’s previously injured knee made sense, but it became a little tiresome seeing Triple pound the knee and apply rest holds. The match definitely had more good than bad. We saw Seth actually land a Phoenix Splash (probably because Triple H was tough enough to take it). Stephanie McMahon got her annual comeuppance of someone accidentally hitting her. Overall good match – the very definition of 3 ½ star affair.
Vs. John Cena (WrestleMania 22)
If there is one match where Triple H’s involvement felt particularly forced, this may have been it. The obvious match was Cena vs. Edge after Edge absconded with Cena’s WWE Championship. But Edge had a barnburner (almost literally) with Mick Foley and turned out more than fine. The match was alright, passable for the main event. But Cena retaining his championship just wasn’t as satisfying as if he won it. This match is really known for the fans vehemently preferring heel Triple H over babyface Cena. (Also, CM Punk was an extra in Cena’s entrance.) I’ve alluded before that it’s not a good sign when there’s no video package to start a big match. In this case, it seems like the culprit is Hunter burying Cena during promos. And he wasn’t even trying! Fans just preferred him over Cena by this point!
Vs. Batista (WrestleMania 21)
On this night, fans had already seen epic (HBK vs. Angle). They had already seen disappointing (Cena vs. JBL). And this match was serviceable. But in a good way. This was ostensibly the platonic ideal of what a Wrestlemania main event should be. New babyface conquers longtime heel and wins the championship in a feel-good moment. The build was great with former stablemates imploding and Triple H trying to manipulate Batista into jumping to Smackdown after winning the Royal Rumble. Yeah, we had seen the formula of a good guy beating a bad guy done better. Yeah, their Hell in a Cell match at Vengeance blew this out of the water. But this list alone has several examples of Wrestlemania headliners falling flat. So sometimes, serviceable works.
Vs. Booker T (WrestleMania 19)
With the terrible build and aftermath, it’s pretty easy to forget: This match is actually pretty good. It’s easy to understand why people don’t like this one. The entire build centered around Triple H dressing down Booker T and bringing up the mistakes he made. But don’t worry, it “wasn’t racism”. It was “about Booker being a WCW guy.” Um, sure Jan. Even if that were true, that is not much better. It’s bad enough Booker T lost a feud that played the race card, but Booker got pinned after that infamous Pedigree that took a dog’s age. Although I think Triple H was motivated by ego, rather than racism, it was still a bad call. Looking past the bad booking, the match is still mostly solid. And we even got to see a Houston Hangover.
Vs. Undertaker (WrestleMania 27)
This was one of the few highlights of a fairly dreary Wrestlemania. Taker and Hunter had both been relegated from active performers to occasional attractions. If these two only had one match (as Undertaker did that year), they were going to make their one match count. The match was truly dramatic and there were some brutal spots, including a rare example of Triple H actually scoring a Tombstone ON the Undertaker. But there was A LOT of resting in between big spots. At the time, I thought this was one of the most overrated matches in Mania history. But its reputation has shifted from stone classic to well-liked match. In other words, it’s gone from overrated to perfectly rated.
Vs. Undertaker (WrestleMania 17)
This was the first showdown between the Game and one of his best Mania opponents. The match felt a little like WWE was pairing the spares since they were the only big names not involved in a big match. But it also made sense since it was the first time these two had a match on a big stage (as opposed to Raw or house shows). This was a pretty wild brawl, though it was a little hard to believe that the ref stayed knocked out for so long. It makes one wonder why they didn’t just make it a no DQ match. Probably thought there were too many in a row… But they still treated it like one! Leaps in logic aside, this was a banger. One of the many reasons Wrestlemania 17 is so fondly remembered.
With Stephanie McMahon vs. Kurt Angle and Ronda Rousey
Besides being one of Triple H’s best Mania matches, this is 100% the best Stephanie McMahon match ever. This was a weird combo – a non-wrestler, two legends who were past their prime, and someone making their debut. In hindsight, it may seem like a foregone conclusion that WWE’s new prospect would win. But the memories of what they did with Sting were fresh in fans’ minds. Luckily, the McMahons took the smart route and made Ronda look like a beast. We even saw some rare intergender action. Triple H and Stephanie played their roles as cowards to a hilt, as Stephanie finally ate an L. Plus, the tag team format ensured that there was no dead space. Plus, it probably ensured the veterans could hold Ronda’s hand to a stellar debut.
Vs. Daniel Bryan (WrestleMania 30)
One could write an entire article about how we landed at this match. After wisely transitioning to make the main event about fan-favorite Daniel Bryan, nobody had to believe Bryan would lose and make it a Triple Threat between Evolution stablemates. But it certainly made Bryan’s climb to the world championship all the more dramatic. Unlike the main event, there was no stipulation so the two just had their ring work to carry the day. Daniel Bryan brought his technical prowess and The Game brought his old-school storytelling in a match that kicked off a great two-part story.
Vs. Shawn Michaels vs. Chris Benoit
It’s pretty easy to see why this match might be a sore spot for some fans. If you can look past the bad history, this is classic storytelling. A scrappy underdog who has paid his dues was trapped between two titans of the business to win his first world title. This was in the thick of what many fans consider the Reign of Terror so seeing Benoit topple him was a feel-good moment, made all the better by Eddie Guerrero joining him with his WWE Championship. After proving why four ways are hard to do, this was the first proper triple threat match, proving those can work. With three talented workers, there was never a dull moment in the entire match. Shawn Michaels bled buckets, there was a table spot and a happy ending. Some people might not like watching Chris Benoit matches, and that’s understandable. But this still stands as one of the best main events in Wrestlemania history.
Vs. Undertaker (WrestleMania 28)
Maybe nobody bought that “end of an era” buildup, but that’s moot when a match is this good. (Though I suppose it was the end of something since H cut his trademark long hair later that summer.) Comparing this match to its predecessor is like comparing the Terminator to T2. Both are great, but one just built on everything that worked. The Hell in a Cell match had lost a little mystique even by this point, making this one of the best matches of its kind in a while. And honestly for a while. I criticized their Mania 27 match for taking too many rests, but this time the “rests” did a much better job selling the damage, especially since they upped the ante big time. Shawn Michaels helped sell this, especially because of his grudge with Undertaker and friendship with Hunter. There are too many great spots to list, including Undertaker eating all the finishers but still going. The match ended with all three men celebrating, and it was well-earned.
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© 2022 Alex deCourville