I have such good memories of NHLPA '93. My dad bought it totally out of nowhere for the Mega Drive and it was one of the few games he ever tried to play. I'm not sure which came first, but either that game or the '94 Winter Olympics was what started my interest in hockey. If watching hockey in the Olympics came first then, that would explain why he randomly bought it
Most recent game I've owned/played is NHL Legacy Edition on 360 - essentially an NHL 16 roster update IIRC. It's decent but, I just never really felt it ever captured the nature of the game the way EA managed to with, say, FIFA.
Pound for pound I feel the 16-bit titles capture it better with their respective technology for the time. They're still super fun to play, I'll switch between any of the titles from 93-98. They've all got their own charms, be it difference in gameplay or just playing with old teams/rosters, although I'm not really keen on '95. I tried revisiting NHL '99 on PS1 but that one felt dated to me - although it still has one of the best OSTs for a sports title ever.
If you want best of both worlds - there's an NHL '94 team/roster mod for Mega Drive/Genesis emulators. NHL 18 is the most recent mod I'm aware of, although I'm sure it'll get another update once Seattle enters the league. Definitely recommend it - it's a fun novelty to play a 25-year old hockey game with modern players and teams like the Golden Nights and Nashville, etc.