Does the DOS version of Transport Tycoon run under Win95/98/ME?
Usually it is possible to get the DOS version running under these versions of Windows, but there’s no guarantee. There should be no need to run the game in “DOS mode”, though this might help if all else fails. The thing which usually prevents the game from running is the sound effect drivers, which cause problems with anything but standard sound card DMA and IRQ settings. If the game won’t work, try installing it with the sound effect driver set to “none”, and you may well get the game working. The music driver is not usually a problem as long as the settings match your card.