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You may already be aware, but unlike professional football and basketball in the US, the professional baseball draft happens at mid-season, in June. Moving it outside the season in OOTP before a season starts or after the season has completed will have the effect of associating the draft with the next uncompleted season rather than the one just completed. But since the new season hasn't started yet, the draft doesn't recognize the new season yet. Hence your problem. Keeping it mid-season avoids all of this trouble.
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