I can't remember if they do have winners play in the evening as a sort of rule, but if not, I'd probably expect Matteo vs Roger to be the evening slot.

It does look like it'll be particularly hard for Roger to progress now - he'll almost certainly have to beat Novak (there would be a chance he could sneak through if Novak won all 3 matches and the other 3 exchanged wins), but even if he did, it would likely end up with those two and Thiem on 2 wins, and then it would then come down to games and sets, and with two 2-0 wins today, Roger's at a disadvantage on that front already.

Their Wimbledon match was an absolute disaster for Matteo, who obviously struggled badly today as well, but I can't see the Italian playing that poorly again, and was probably largely nerves (like that Centre Court match), so while maybe not enough to win, I would expect some sort of response from Berrettini on Tuesday.