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| 1st(1st leg) | Inter | - | Bologna FC | 2:1 (2:0) | ||
| 2nd (2nd leg) | Bologna FC | - | Inter | 1:3 (0:1) | ||
| 1st(1st leg): 30/11/1999 | 2nd (2nd leg): 15/12/1999 | Winner: Inter | ||||
| 1st(1st leg) | Cagliari Calcio | - | Parma AC | 1:0 (0:0) | ||
| 2nd (2nd leg) | Parma AC | - | Cagliari Calcio | 2:2 (1:2) | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 15/12/1999 | Winner: Cagliari Calcio | ||||
| 1st(1st leg) | SSC Napoli | - | Juventus | 1:3 (1:2) | ||
| 2nd (2nd leg) | Juventus | - | SSC Napoli | 1:0 (1:0) | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 16/12/1999 | Winner: Juventus | ||||
| 1st(1st leg) | AC Perugia | - | ACF Fiorentina | 1:0 (1:0) | ||
| 2nd (2nd leg) | ACF Fiorentina | - | AC Perugia | 2:0 (2:0) | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 15/12/1999 | Winner: ACF Fiorentina | ||||
| 1st(1st leg) | Ravenna Calcio | - | Lazio Roma | 1:1 (0:0) | ||
| 2nd (2nd leg) | Lazio Roma | - | Ravenna Calcio | 4:1 (1:0) | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 15/12/1999 | Winner: Lazio Roma | ||||
| 1st(1st leg) | AS Roma | - | Piacenza Calcio | 0:1 (0:1) | ||
| 2nd (2nd leg) | Piacenza Calcio | - | AS Roma | 0:3 (0:0, 0:1) aet | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 15/12/1999 | Winner: AS Roma | ||||
| 1st(1st leg) | AC Venezia | - | Udinese Calcio | 3:0 (2:0) | ||
| 2nd (2nd leg) | Udinese Calcio | - | AC Venezia | 2:0 (0:0) | ||
| 1st(1st leg): 01/12/1999 | 2nd (2nd leg): 15/12/1999 | Winner: AC Venezia | ||||
| 1st(1st leg) | Atalanta | - | AC Milan | 3:2 (0:1) | ||
| 2nd (2nd leg) | AC Milan | - | Atalanta | 3:0 (1:0) | ||
| 1st(1st leg): 02/12/1999 | 2nd (2nd leg): 14/12/1999 | Winner: AC Milan | ||||
