Hi, I've had a similar issue. Transfer Deadline Day doesn't skip completely, but does skip 2-3 hours at a time meaning I miss a lot of information and events. Just now I put in a bid for a player and offered a contract only for the game to skip a few hours until after the deadline. I've also seen other players I was tracking have offers accepted and join new clubs without me getting the chance to put a bid in myself.
I've uploaded a save game from midway through deadline day under the name "latics roma".