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One thing I had to do in the past that might work, was hit the button twice.
When I was creating a fictional league and filling the teams, for some reason I had to do it twice for my lowest level of minors. The other levels all filled fine but for some reason I had to do that one twice.
I hit it once, checked the teams to see how many players were there, (not enough) then went back to set up, hit fill button again, then when I checked they were fine.
Worth a try maybe.
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