The 10 Greatest WWE Matches of Triple H’s Career

Triple H celebrated his 25th Anniversary of making his WWE debut on this week’s Friday Night SmackDown. Years before his 14 reigns as world champion began, the former WCW midcarder known as Terra Ryzing made his debut for World Wrestling Federation as the Connecticut blue blood Hunter Hearst Helmsley. Over the years he would go on to be a pillar of the WWE while leading factions like D-Generation X and Evolution while having classic feuds with The Rock, “Stone Cold” Steve Austin, Shawn Michaels, The Undertaker, Batista and John Cena.

Which such a long and illustrious career, it’s hard to pick out just ten matches that stand the test of time as Triple H’s all time greatest, but that’s what I’ve set out to do. Surely there are several other matches which could be added to this list and many of them were likely part of an early draft of this article at one point or another.

In chronological order, I present to you my own personal top ten matches in the career of Triple H.

Triple H vs. The Rock (SummerSlam 1998)

While both The Rock and Triple H were rising stars before this match, this was the bout that really seemed to set the stars on the path to super-stardom as future headliners. 

Feuding over the WWE Intercontinental Championship, the two men wrestled in a ladder match at the same venue where Razor Ramon and Shawn Michaels had made the match famous four years earlier. SummerSlam ’98 was headlined by Steve Austin taking on The Undertaker, but this was the match that stole the show. 

Triple H vs. Cactus Jack (Royal Rumble 2000)

As the year 2000 began, Mick Foley’s career was starting to wind down. His feud with Triple H was supposed to culminate with a career ending Hell In A Cell match at February’s No Way Out PPV.

Instead, Foley was called back for a fatal four-way WrestleMania main event match that would go down as one of the worst main events in the history of WWE’s biggest show. It paled in comparison to the two matches that Foley had in the two months prior with Triple H, the aforementioned No Way Out bout, as well as January’s Royal Rumble Street Fight.

The Street Fight at the Royal Rumble is easily the best match among the two and a must-watch for anyone who hasn’t seen it (or even if you have, if you haven’t seen it in a long while). Foley (as Cactus Jack) and Triple H went to places that Hunter hadn’t been previously, including barbed wire and thumbtacks. It was a WWE Championship match the likes of which had never been in Madison Square Garden before. 

Triple H vs. Chris Jericho (Fully Loaded 2000)

Chris Jericho and Triple H headlined WrestleMania 18 in 2002 in a championship match that didn’t measure up to expectations. If you want to see a match between them that did, watch their match at Fully Loaded in 2000. It’s not a championship match, but it is a Last Man Standing match. 

Just under one year into his WWE tenure, Jericho was still red-hot as a babyface. Triple H was in the midst of the best run of his career, arguably the top heel in the business that was having great matches month after month. 

Early that year in April while Triple H was the world champion, he and Jericho had a match on RAW that Jericho briefly won and was declared the new world champion. He received an insane pop from the crowd that night. However, that decision was reversed. Fast forward three months and although there was no title on the line, it exceeded anything the two had done prior. Jericho would have to wait another year and a half before winning the world championship for the first time, but this is an excellent match that is well worth going out of your way to watch. 

Triple H & Steve Austin vs. Chris Jericho & Chris Benoit (RAW: May 21st, 2001)

One of the most famous television tag team matches in WWE history for two reasons: the quality of the match, as well as the fact that Triple H tore his quad toward the end of the match and continued to work through it. 

Hunter and Austin were wrestling as the “Two Man Power Trip” and were the reigning WWE Tag Team Champions. On this night, Jericho and Benoit would capture the titles in San Jose.

Triple H’s injury in this match led to one of the best runs of his career being cut short. He’d return the following January and begin his march, as a babyface, to a world championship victory over Chris Jericho at WrestleMania 18. Always better as a heel, Hunter’s heel turn would come soon after that. 

Triple H vs. Shawn Michaels (SummerSlam 2002)

For fans who watched wrestling in the 1990s and early 2000s, nobody ever expected to see Shawn Michaels in a wrestling ring again. Having last performed at WrestleMania 14 in 1998, Michaels made his highly anticipated return to the ring at SummerSlam 2002 to face his former DX partner, Triple H.

This match was built up expertly throughout the summer that year. Michaels was attacked brutally in a parking lot and security footage was eventually uncovered to reveal it was Triple H who was the attacker. Michaels was shocked that his former best friend would do such a thing.

With Michaels wrestling for the first time in over four years, expectations were cautiously optimistic heading into the match. However, Triple H was the perfect man to put in there with HBK for his big return, and the two put together an all time classic that has stood the test of time. 

Triple H vs. Shawn Michaels (RAW: December 29th, 2003)

Out of all of the famous matches between these two, this one sometimes gets forgotten. 

However, it features Shawn Michaels wrestling in front of his hometown crowd in San Antonio against his arch nemesis with one more chance at a world championship. The final RAW of 2003 saw the year go out in fantastic fashion as they had another classic, with a white hot crowd eager to see their hometown kid capture the WWE’s top prize once more.

The two had more than a half hour of TV time in an era where that was certainly rare in WWE. The match is never dull, and the crowd going ballistic for the false finishes in the final moments really puts it over the top. No gimmicks, just a great old school match between two of the all time greats. While the ending throws the crowd for a loop, the match itself stands up just as well today as it did over 16 years ago. 

Triple H vs. Shawn Michaels vs. Chris Benoit (WrestleMania XX)

The match is more than a little bit difficult to watch today for obvious reasons, but it’d be a mistake to not put this bout into the top ten list.

Personally, I’m not a huge fan of triple threat matches, but this one stands above the rest. When you consider the great in-ring history that Michaels and Triple H had heading into this bout (including the aforementioned singles match from RAW in December that heated up their feud once more), and you add a ring technician like Chris Benoit to the match, you’re bound for greatness. And that’s exactly what we got. 

Triple H vs. Batista (Vengeance 2005)

Batista defeated Triple H at WrestleMania 21 for the World Heavyweight Championship. The match had a long build, going back to the two teaming up in Evolution. Batista’s victory at WrestleMania was a star-making moment, no doubt about it.

However, that match pales in comparison to the Hell In A Cell match the two had just a couple of month’s later at June 2005’s Vengeance PPV event, this time with Batista as the champion heading in. This is arguably Batista’s greatest match of his career, and for my money, definitely one of Triple H’s top ten bouts. 

Triple H vs. The Undertaker (WrestleMania 28)

Some would say that their match at the previous year’s WrestleMania was the better match, technically speaking, and I would probably agree.

However, the Hell In The Cell “End of an Era” match that Undertaker and Triple H had at WrestleMania 28 just had a little bit more pomp and circumstance to it (as well as the involvement of Shawn Michaels) which takes it up a notch for me. The moment at the end of the match where the three stars walked up the entranceway together and stood next to each other looking out at the crowd is an iconic WrestleMania moment. 

Triple H vs. Daniel Bryan (WrestleMania XXX)

WrestleMania XXX was an event that served to be Daniel Bryan’s crowning moment. He became the undisputed world heavyweight champion in the main event, defeating Randy Orton and Batista in the process.

However, in order to get there, he had to defeat Triple H earlier in the night. The match was the result of a several months long story with Bryan constantly trying to overcome The Authority, who didn’t see him as world championship material. There was a grain of reality in that storyline as well, and truth be told, WWE didn’t initially have Bryan in mind for the main event of this show. And in fact, Triple H was supposed to wrestle CM Punk at WrestleMania XXX.

However, following Punk’s exit from the company and Bryan’s continued ascent to the top of the card as the result of the fan’s getting behind him in a way not seen since the heyday of Steve Austin and The Rock, WWE’s hand was forced. The Triple H vs. Bryan match ended up being a classic encounter, and to date, Triple H’s last great WrestleMania performance. 

What are your own favorite Triple H matches? Let us know in the comment section below or drop me a message on Twitter, @ryandroste.