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| 1st(1st leg) | AC Venezia | - | Bologna FC | 2:2 (2:1) | ||
| 2nd (2nd leg) | Bologna FC | - | AC Venezia | 0:1 (0:0) | ||
| 1st(1st leg): 26/08/2000 | 2nd (2nd leg): 06/09/2000 | Winner: AC Venezia | ||||
| 1st(1st leg) | Cosenza Calcio | - | US Lecce | 0:2 (0:1) | ||
| 2nd (2nd leg) | US Lecce | - | Cosenza Calcio | 1:1 (1:0) | ||
| 1st(1st leg): 26/08/2000 | 2nd (2nd leg): 06/09/2000 | Winner: US Lecce | ||||
| 1st(1st leg) | Brescia Calcio | - | Vicenza Calcio | 2:1 (1:0) | ||
| 2nd (2nd leg) | Vicenza Calcio | - | Brescia Calcio | 4:5 (2:0, 2:1, 2:1) pso | ||
| 1st(1st leg): 26/08/2000 | 2nd (2nd leg): 06/09/2000 | Winner: Brescia Calcio | ||||
| 1st(1st leg) | Salernitana Sport | - | AC Perugia | 1:0 (1:0) | ||
| 2nd (2nd leg) | AC Perugia | - | Salernitana Sport | 2:1 (1:1) | ||
| 1st(1st leg): 26/08/2000 | 2nd (2nd leg): 06/09/2000 | Winner: Salernitana Sport | ||||
| 1st(1st leg) | Torino FC | - | AS Bari | 2:1 (1:0) | ||
| 2nd (2nd leg) | AS Bari | - | Torino FC | 0:0 (0:0) | ||
| 1st(1st leg): 27/08/2000 17:00 | 2nd (2nd leg): 06/09/2000 | Winner: Torino FC | ||||
| 1st(1st leg) | Piacenza Calcio | - | Hellas Verona | 2:1 (0:0) | ||
| 2nd (2nd leg) | Hellas Verona | - | Piacenza Calcio | 2:2 (1:0, 2:1) aet | ||
| 1st(1st leg): 27/08/2000 19:45 | 2nd (2nd leg): 06/09/2000 | Winner: Piacenza Calcio | ||||
| 1st(1st leg) | Atalanta | - | Reggina Calcio | 2:0 (1:0) | ||
| 2nd (2nd leg) | Reggina Calcio | - | Atalanta | 0:1 (0:0) | ||
| 1st(1st leg): 27/08/2000 19:45 | 2nd (2nd leg): 06/09/2000 | Winner: Atalanta | ||||
| 1st(1st leg) | Sampdoria | - | SSC Napoli | 1:0 (1:0) | ||
| 2nd (2nd leg) | SSC Napoli | - | Sampdoria | 0:0 (0:0) | ||
| 1st(1st leg): 27/08/2000 20:00 | 2nd (2nd leg): 07/09/2000 | Winner: Sampdoria | ||||
