@reaver013 you can only play dos games in recalbox, see https://github.com/recalbox/recalbox-os/wiki/How-to-use-DOSBox-to-emulate-DOS-games
But late 90's / early 2000's are usually Windows 95-98 games and no, you can't play those
Some of those games might be existing on other platforms though, I seem to remember the Timo & Pumba game was released on Snes or Megadrive