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