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Well you can sort of do what you're looking for. You can start a historical league in 1990. Then go into game setup, and there's a button that says something like "Reset and release all players and schedule initial draft". This will schedule an initial draft. Then from there on out you should get amateur draft with the rookies from each season being a part of the draft from year to year.
You can click an option to fill in the minor leagues with fictional players, or use ghost players (essentially players that don't show up, but the game still functions as if they were there).
To get a full draft where you had a complete world from 1990 (majors to minors) would be much more difficult and I'm not sure how possible. I do know that there's a few modified databases out there that may do something similar to this, but I can't help you out there.
Hope that helps some! The majority of what you want to do is very possible!
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