DL 5205 then DL 1669 at Detroit
Madison → Detroit → New York LaGuardia
Timetable, Detroit time
12:16DL 5205 from Madison at the gate
12:15DL 1669 to New York LaGuardia leaves the gate
23 h 59 apart on the timetable, overnight
DL 1669 leaves 23 h 59 after DL 5205 arrives on the timetable: more than half a day, so not a connection we count.