 |
 |
|
|
| 1st(1st leg) | Sampdoria | - | Bologna FC | 0:2 dec. | ||
| 2nd (2nd leg) | Bologna FC | - | Sampdoria | 2:0 (1:0) | ||
| 1st(1st leg): 12/10/1999 | 2nd (2nd leg): 26/10/1999 | Winner: Bologna FC | ||||
| 1st(1st leg) | Cagliari Calcio | - | Genoa CFC | 3:1 (1:0) | ||
| 2nd (2nd leg) | Genoa CFC | - | Cagliari Calcio | 1:4 (0:1) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 28/10/1999 | Winner: Cagliari Calcio | ||||
| 1st(1st leg) | SSC Napoli | - | AS Bari | 1:0 (0:0) | ||
| 2nd (2nd leg) | AS Bari | - | SSC Napoli | 1:1 (0:0) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 28/10/1999 | Winner: SSC Napoli | ||||
| 1st(1st leg) | Pescara Calcio | - | AC Venezia | 0:0 (0:0) | ||
| 2nd (2nd leg) | AC Venezia | - | Pescara Calcio | 1:0 (0:0) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: AC Venezia | ||||
| 1st(1st leg) | Ravenna Calcio | - | Hellas Verona | 2:1 (1:1) | ||
| 2nd (2nd leg) | Hellas Verona | - | Ravenna Calcio | 1:2 (0:1) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: Ravenna Calcio | ||||
| 1st(1st leg) | Reggina Calcio | - | Piacenza Calcio | 0:0 (0:0) | ||
| 2nd (2nd leg) | Piacenza Calcio | - | Reggina Calcio | 2:0 (1:0) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: Piacenza Calcio | ||||
| 1st(1st leg) | Ternana Calcio | - | AC Perugia | 1:2 (0:1) | ||
| 2nd (2nd leg) | AC Perugia | - | Ternana Calcio | 1:1 (0:1) | ||
| 1st(1st leg): 13/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: AC Perugia | ||||
| 1st(1st leg) | Atalanta | - | Torino FC | 3:1 (0:1) | ||
| 2nd (2nd leg) | Torino FC | - | Atalanta | 2:1 (1:1) | ||
| 1st(1st leg): 14/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: Atalanta | ||||
