DOS Games made for DOS require an emulator to run on Windows. Use DOSBox or a frontend like D-Fend Reloaded and read this guide to play DOS games on your Windows PC.
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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