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DOS games can't run on Windows. You need a DOS emulator like DOSbox or D-Fend Reloaded. Follow these instructions to play DOS games on Windows 10 or later systems.
The Commissioner's Disk was released in 1988. It was an advanced player, stadium and team editor, able to make deeper changes, such as skin tone (in the original version, one had to clone a black player in order to create a new black player). It also featured a schedule generator, as well as advanced stat analysis, and so forth.
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