FR 5322 then AV 2506 at Madrid
Milan → Madrid → Lisbon
Timetable, Madrid time
19:45FR 5322 from Milan at the gate
18:00AV 2506 to Lisbon leaves the gatealso EK 4859, AD 7273, S4 8963
22 h 15 apart on the timetable, overnight
AV 2506 leaves 22 h 15 after FR 5322 arrives on the timetable: more than half a day, so not a connection we count.