We’ve reached that stage in the transfer window where we’ll find out if all the “should”s and “could”s will become reality.

Perhaps unsurprisingly, considering their managerial issues, Chelsea are involved in a lot of these, embroiled in a strange situation with Milan in Italy.

Both clubs are currently after Bernard, whose preference would be a move to Serie A, but Leonardo, their new technical director, has yet to give the green light on the deal.

At the same time, the Blues are considering making a move for one of Milan’s players, Pepe Reina, should Thibaut Courtois end up getting his wish and transferring to Real Madrid to see his children more regularly.

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Chelsea have set a Tuesday deadline for the Bernard deal, which we’ve covered in the past, but Gazzetta dello Sport state that should the Italians sell one of their forwards (Niko Kalinic or Carlos Bacca) on Monday, then the Brazilian’s arrival could be done in the next 24 hours.

As for the Spanish goalkeeper, he’s made it clear he’d rather stay in Milan to provide competition for Gianluigi Donnarumma, but a lot will depend on how much the Blues are ready to pay for him.

Considering the Serie A side’s issues with FFP, making a €6-8m profit on a 35-year-old they only signed this summer could be too good to refuse.

The next few days will be extremely revealing, as Chelsea’s window could end up with two new arrivals just like it could finish with neither of the players heading to Stamford Bridge.