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It seems you don't have enough players in the minors. First thing I'd try is enabling 'Ghost Players', which is somewhere in the Game Setup options (don't have the game open right now, sorry). Ghost Players are fake players created just before a minor league game starts and are deleted just after a minor league game ends, and their purpose is to fill in exactly the kind of roster gaps you seem to have in your league. Hopefully that does the trick; otherwise you'll probably need to fill your minor leagues with fictional players.
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