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I've been doing this for hours now! Making sure I mark any duplicates etc. - I've just finished doing all of the Championship and Bundesliga.. gonna do the Brasileirao transfers now. Thankfully I have an up to date pre-DLC file so I'm just gonna clear each Brazilian team of all their players and add them one by one. Would be quicker I think.
Then I'm going to copy all of my 'Edit Players' to replace duplicates, freeing up the Edit slots.
One good thing about this update is now, we can use duplicate national team players as spares because there won't be another squad file to mess it up.
Is the players on free agent missing after you update the dlc? Or is it still there?
2. Screw that, there's probably 500 transfers to do.
He didn't fully explain it.
If you say "no", all it takes to get the new transfers is to go to the "Transfer" part in Edit mode, then hit triangle once to default the transfers on each league that you'd like to update.
In my case, I wanted to keep the Championship as is, so hit triangle on everything else, updating everything in under a minute.