Milan managed to sneak two exits under the Premier League transfer deadline, sending Fode Ballo-Toure on loan to Fulham and Divock Origi to Nottingham Forest.
The Serie A market closed at 19.00 UK time (18.00 GMT), but they could continue to sell or loan out players.
Even then, they left it extremely late, because it took several hours after the deadline in England at 23.00 UK time (22.00 GMT) for them to be made official.
Under the English rules, if clubs submit the paperwork in time, the details can be filled in later and transfers completed anyway.
It was only past midnight that it emerged Milan had sent full-back Ballo-Toure to Fulham on a one-season loan.
He had been in talks with Fulham last week, as well as Werder Bremen and Bologna, but struggled to agree personal terms.
Meanwhile, after undergoing his medical in the afternoon, Origi got his move to Nottingham Forest right down to the wire and it was only confirmed at 00.40 UK time.
This is reportedly a loan with Nottingham Forest paying his full salary, plus an option to make it permanent for €5m.