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I can't speak for v14, as I just recently bought it and haven't played any postseason with it yet...
But with v13, if you are between playoff series you can go into commish mode and under the player editor tab you can mark off a checkbox for "playoff eligible". After that, you should be good to move them onto the playoff roster, assuming your injured guys are then removed.
I'm not quite sure how closely OOTP mirrors actual MLB.. as there always seems to be injury exceptions that happen in MLB that aren't allowed in OOTP. For instance, I'm pretty sure mid-series injury replacements are allowed with commissioner approval in MLB, but that doesn't seem to reflect in OOTP. If the series is started, you are stuck.
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