1st(1st leg) AC Milan - Inter 2:3
2nd (2nd leg) Inter - AC Milan 1:1
1st(1st leg): 12/01/2000 2nd (2nd leg): 27/01/2000 Winner: Inter
1st(1st leg) AS Roma - Cagliari Calcio 0:1
2nd (2nd leg) Cagliari Calcio - AS Roma 1:0
1st(1st leg): 12/01/2000 2nd (2nd leg): 25/01/2000 Winner: Cagliari Calcio
1st(1st leg) Juventus - Lazio Roma 3:2
2nd (2nd leg) Lazio Roma - Juventus 2:1
1st(1st leg): 13/01/2000 2nd (2nd leg): 26/01/2000 Winner: Lazio Roma
1st(1st leg) AC Venezia - ACF Fiorentina 0:0
2nd (2nd leg) ACF Fiorentina - AC Venezia 1:1
1st(1st leg): 13/01/2000 2nd (2nd leg): 26/01/2000 Winner: AC Venezia