Stealing Steve's idea in my attempts to get more discussion going in the wrestling sections.
Triple H is a guy who is very highly rated by many on the internet, and he's been around a long time, so I thought he would be a good pick for the next installment of this. Basically list the best Triple H match from every year he has been active in WWE. Preferably give a few notes as to why you believe this was his best of the year, but this isn't essential.
I'll start with 1997, but even from this year I've not seen too much.
1997: vs Cactus Jack - RAW Hardcore Match - This is a really fun match and I really enjoy Foley. Not seen much HHH stuff from 97 but this is the best I've seen.
1998: vs The Rock - Summerslam 1998 Ladder match - Again, not seen a lot from this year, but I remember this being a very good ladder match. Needs a rewatch though.
1999: vs Vince McMahon - Armageddon No Holds Barred - 1999 was pretty terrible for good matches in general. HHH vs Kane at Mania is an anti-classic. The Vince match was at least a lot of fun, with Vince going to great lengths to make the match entertaining as always.
2000: vs Cactus Jack - Royal Rumble Street Fight- This is easily the toughest year. He produced a lot of very good stuff with Foley, Rock, Jericho, Austin, but for me the Rumble match just gets the nod over other great matches such as the Jericho LMS and the Rock Ironman. Great brawl with an epic finish.
2001: vs Steve Austin - No Way Out 3 Stages of Hell - He missed most of 2001 with an injury of course, but he was still able to put on a few great matches before the injury, ironically including the match he was injured in. This one was off the charts though. It will easily make my top 10 in the "Top 100 WWE matches of the decade" list. This is a contender for his best match.
2002: vs Shawn Michaels - Summerslam Unsanctioned Match - Another truly great one. The whole Michaels return angle was great and this was a hell of a brawl.
2003: vs Shawn Michaels - New Years Eve RAW - lol this is where it starts to go to shit. Most of his PPV matches were god awful, although he was facing some pretty limited guys. Have to go with the RAW match against HBK, which was actually really good I thought. Their second best match maybe?
2004: vs Chris Benoit vs Shawn Michaels - Wrestlemania XX - Wow, Shawn Michaels in HHHs best match 3 consecutive years. The 2003 one pretty much wins by default though, and this was more about Benoit of course. If not 5*, its very close.
2005: vs Batista - Vengeance Hell in a Cell - Don't remember their 2nd match, but I wasn't a fan of their Mania encounter, which bored me. The Hell in a Cell was surprisingly great though. Lot of brutality and Batista looked fucking great.
2006: vs John Cena - Wrestlemania 22 - The DX return made good matches a thing of the past for a lot of this year, but even if overrated and helped a lot by the crowd, the WM match was very good.
2007: vs Randy Orton - No Mercy Last Man Standing - This was brilliant. I was gutted by Cena's injury, but they went out there and produced one of the best LMS matches I've seen. So much drama and intensity.
2008: vs Randy Orton vs John Cena vs JBL - Backlash Elimination match - More HHH/Orton greatness, as strange as that sounds now. The match was good at first, but when it became one on one it became great, and really had an epic feel to it.
2009: w/Michaels vs Legacy - Summerslam - Can't think of anything notable he's done 1 on 1, but the Summerslam tag was surprisingly good and made Legacy look impressive. I didn't like the Chamber he was in.
You don't have to put in as much detail as that, but go!~
EDIT: HOLY SHIT AT ALL THE GIMMICK MATCHES