I have played transport tycoon on many differnt system configurations and can confirm that it works well under DOS (assuming drivers are correctly installed) or Windows 95/98. The Deluxe version comes in two editions - Winows and DOS. The Windows one doesn't run on DOS, obviously, the DOS one will run on Windows 95/98 (and probably ME).
Windows XP requires the Windows Transport Tycoon Deluxe + TTDPatch OR OpenTTD. Windows 2000 is probably the same as XP. Hope this helps someone.
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