Ganja Farmer...

Chips Challenge for Windows, Sim City 3000, Age of Empires 2, Super Mario Bros. 3, Command & Conquer Red Alert 2 (Technically not pre-2000 because it was released in 2000.)

Infantry. My first online multiplayer game. Somehow I made it into a squad that got 2nd place in the seasonal tournament and also had arguably the best player in the whole game. I didn't play in the matches but I was in the squad!

Lords of the Realm 2, the OG X-Com trilogy, Total Annihilation, Dark Reign, Civ II Test of Time

Right on Y2K was NFS Porsche Unleashed aka Porsche 2000. As long as you play the PC version it's an amazing game and there are a few graphics enhancing mods too.