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This sort of issue arises because OOTP keeps having the 60-day DL in operation during the off-season. That's not how it works in real life. In real life, by rule all players on the 60-day DL have to be reinstated from it no later than the day the reserve (40-man) roster lists are filed, usually Nov. 20th. From that point on there is only the 40-man roster. The DLs don't start up again until early in spring training.
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