That's a tough question. Triple H had so many great matches, but I really liked his HIAC match with the Undertaker at Wrestlemania. That was basically perfection, and should have been Taker's last match in my opinion.
Very tough call for me between No Way Out with Austin and Hell in a Cell with Undertaker. I went with Austin just because it's Austin but I still can't be sure. His Survivor Series 2000 match with Austin should also get a mention in this catalogue.
Vs Rock at Summerslam 98 and Vs HBK at Summerslam 02 would round up for me it's hard for me to pick.
He beat Rock in their best match together but it was necessary for Hunter as Rock was already growing in popularity with the general audience to move up the ladder(Puns i know) and then took the loss to Shawn in his first match back in a grueling non sanctioned bout like a boss while still walking out by the end of it leaving a cliffhanger, Quality storytelling performances but mostly the two that stand out more for me personally.
Vs Batista at Vengeance was a fantastic way to send the Evolution breakout star off to bigger things on his own after losing HIAC in the rubber match as well.
Vs HBK on Raw Dec 03 was a great renewal of their on and off rivalry that Kickstarted a RTWM storyline soon to involve Benoit later on.
Vs Undertaker at WM27 which is overlooked a lot but i preferred this over their WM28 HIAC match.
He has had numerous great ones from SS 98 to WM 30. For me his best match is with Foley at RR 2000. I consider this one of the best matches ever. A match that transfixed the crowd, it had several bone chilling moments. The spot where Foley runs into a chair shot to the head just to show his fearlessness or Triple H following the handcuffed Foley with vicious chair shots or when Triple H goes nuts after Foley kicks out of the Pedigree. It's simply the best hardcore wrestling match ever.
Not on the list, but when HHH was feuding with Ric Flair, they had a cage match on Taboo Tuesday that was absolutely tremendous, full of blood and violence, and probably one of the best heel HHH matches ever. He was just vicious in that match. I'd have it on this list, and it's pretty underrated.
Personally though I adored the match with Daniel Bryan, the HIAC at Mania with Taker I always loved, and the HBK match in 2002 at Summerslam
I might be a bit biased because I was at the show, but the Street Fight with HBK at SummerSlam 2002 was amazing. As great as the crowd comes off on TV for that match, it was a MILLION times better and louder at the show live. I'll never forget that night. The entire show as awhole was fantastic, but that Shawn/Trips match blew the roof off of the Nassau Coliseum. Great job by HHH in that match by working with a guy who was gone for 4.5 years. And amazing job by Shawn to literally look like he never missed a day in the ring, which is ridiculous considering he almost missed a full half-decade in the ring by that point.
Besides that, there's the Street Fight with Cactus Jack at the 2000 Rumble. The 3 Stages of Hell Match with Austin. The HIAC WM Match with Taker. The last RAW match of 2003 vs. Shawn in San Antonio when they did the Dusty Finish and had everyone thinking that Shawn won the Title in his hometown. There's also a forgotten, underrated match with Shawn on the 5/13/96 RAW when Shawn was Champion. The Street Fight vs. Cactus Jack on the 9/22/97 RAW at MSG. The 1997 KOTR Finals Match vs. Mankind.
The first Elimination Chamber Match at Survivor Series 2002 because he went the entire length of the match and the majority of that time he had a crushed larnyx when RVD landed on his throat on the way down from his Frog Splash, but that match was great, too. Triple H gets shit on alot and we all know why, but he's had his fair share of excellent matches in his career for sure.