1. NHL 98 (PS1) - Easily the game I played the most of as I played very little of NHLs 99-2004. Felt it was better than 99-01 by a mile hence why I kept going back to it despite owning copies of the other 3. The intro video and soundtrack are classic. When it came out in the Fall of '97 the presentation was mind-blowing. This is and will likely always be my favorite all-time NHL game.
2. NHLPA 93 (SNES) - Sorry but neither me nor my friends owned the fabled NHL 94 so NHLPA 93 was our jam. If you could stop yourself from scoring the wrap-around or the "half-wrap" we called it (cutting out of the corner across the net), the game was challenging vs. the AI.
3. NHL 2014 (PS3) - The peak of the PS3/Xbox 360 era. HUT was still fun and the game really had no flaws and was the least buggy of the recent games (to this day NHL 13 is my most disliked NHL due to how buggy it was).
4. - NHL 2005 (PC) - Was the first NHL I played consistently since the above mentioned NHL 98. On PC their was no options to create players or edit players that year so whoever was in the game was in the game (pardon the pun). The GM mode had a "keeping costs down" benefit to player salaries (no salary cap in that game) and it was a fun experience.
5. - NHL 95 (SNES) - First NHL that you could create players and move players. Spent way too much time creating teams and players. Gameplay I felt was improved from the earlier NHLs.
6. - NHL 2011 (PS3 and Xbox 360) - HUT was in it's infancy but still a bit of fun. The peak of my EASHL participation, had a team with 4-5 local friends. We weren't good but was a lot of fun. Felt the overall game was solid top to bottom.
7 - NHL Open Ice (Arcade) - Going off the board with a stand-up arcade game in NHL Open Ice. Basically NBA Jam for hockey, I always used the Bruins I can still hear the announcers screaming "Ranford" over and over.
8 - EA NHL 3 on 3 Arcade. (PS3) I booted up my old PS3 the other day and was pleasantly surprised to see this game still installed on the drive. Just a fun NHL game that played well and didn't require any sort of time commitment and easy to play.
9 - NHL Stanley Cup (SNES) - Was glitchy and you could score some really strange goals, but used the SNES's Mode 7 hardware to it's fullest. Pretty impressive presentation for its time.
10. - NHL 16 (PS4)- The best NHL of the PS4 era. Solid all around and for my money the best HUT experience because it predates the "synergies" that they added to NHL 17 and onward.
HM - NHL 2009 (Xbox 360) - The first NHL I owned from the PS3/Xbox 360 era and was a decent game overall. No major complaints.
Worst - NHL 13 (PS3) - My goodness how much I despised this game. Between the glitches, the system lock-ups, the terribly implemented dynamic skating system, the brutal AI, etc. just an overall awful game. I rarely get upset playing a video game but this one had me tossing my controllers all over the living room.