not much form the 90s has aged well
Even just in terms of video games lots of stuff from the 90s has aged just fine.
Most Super Nintendo and Sega Genesis stuff is still as good (or as bad) as it was in its heyday as 8/16-bit pixel graphics are a little more time-proof than early 3d models and chunky polygons. And most of the first party N64 library is still good. Mario 64, both Zeldas, Mario Kart, Star Fox... Even some of the sports games are still solid like All-Star Baseball or NBA Hangtime. The N64 quartet of THQ/AKI wrestling games (WCW World Tour & Revenge, and WWF Wrestelmania 2000 & No Mercy) are half good on nostalgia and half good on actual quality/care.
The early N64 and PS1 era of stuff does have limitations because of how harsh the transition to the new technology was, but NHL 99's flaws aren't from a crafting/technical standpoint, mostly from a control and play point of view. The game is stiff, sluggish, and suffers for the lack of puck control and adaptable shooting/skating. It's difficult to complete passes and play fluidly and in the game I played (which ended up as a 10-8 final) most of my offence and goals were off of breakaways and odd-man rushes where a puck squirted loose from the crowd and I just turboed up the ice to snatch it and get in clean because the opposing d-men played up too aggressively. And on the other end most goals I gave up were because the puck would be turned over and by the time I switched to a defender he was in no place to find an angle to take out the shooter.
After that game as much as I think I'd enjoy the silliness of the retro rosters, awkward graphics, and laughable plays, I don't think I could sit through 60+ minutes of it just to watch or craft an interesting post/thread about.