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When you look at the playoffs teams in the transaction menu you should have an active roster drop down and a playoff roster drop down. This should also be in the player list screen.
Are you looking at active roster or playoff roster?
Have you tried turning off Playoff Roster Eligibility Rules. I do not remember where the option is but it exists.
I am wondering if the different years you imports are not registering and the game thinks that none of the players are playoff eligible.
When does the 1909 season end? Is it before the August 31st(?) Playoff roster deadline? That may also be the culprit.
Good luck,
Tom (LP)
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