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| 1st(1st leg) | SSC Napoli | - | Cosenza Calcio | 3:0 (0:0) | ||
| 2nd (2nd leg) | Cosenza Calcio | - | SSC Napoli | 0:2 (0:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: SSC Napoli | ||||
| 1st(1st leg) | ACF Fiorentina | - | Parma AC | 1:0 (0:0) | ||
| 2nd (2nd leg) | Parma AC | - | ACF Fiorentina | 0:1 (0:1) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: ACF Fiorentina | ||||
| 1st(1st leg) | Bologna FC | - | AC Reggiana | 4:1 (2:1) | ||
| 2nd (2nd leg) | AC Reggiana | - | Bologna FC | 1:0 (0:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Bologna FC | ||||
| 1st(1st leg) | Modena FC | - | Lazio Roma | 0:0 (0:0) | ||
| 2nd (2nd leg) | Lazio Roma | - | Modena FC | 1:3 (1:1) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 13/09/1990 | Winner: Modena FC | ||||
| 1st(1st leg) | AC Cesena | - | US Cremonese | 4:3 (2:1) | ||
| 2nd (2nd leg) | US Cremonese | - | AC Cesena | 2:0 (1:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: US Cremonese | ||||
| 1st(1st leg) | Sampdoria | - | Brescia Calcio | 1:1 (0:1) | ||
| 2nd (2nd leg) | Brescia Calcio | - | Sampdoria | 0:4 (0:1) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Sampdoria | ||||
| 1st(1st leg) | Hellas Verona | - | Torino FC | 0:4 (0:1) | ||
| 2nd (2nd leg) | Torino FC | - | Hellas Verona | 0:1 (0:1) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Torino FC | ||||
| 1st(1st leg) | AC Monza | - | Inter | 0:1 (0:0) | ||
| 2nd (2nd leg) | Inter | - | AC Monza | 2:1 (1:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Inter | ||||
| 1st(1st leg) | Juventus | - | Taranto FC | 2:0 (1:0) | ||
| 2nd (2nd leg) | Taranto FC | - | Juventus | 2:1 (1:1) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Juventus | ||||
| 1st(1st leg) | Udinese Calcio | - | Pisa SC | 0:1 (0:0) | ||
| 2nd (2nd leg) | Pisa SC | - | Udinese Calcio | 1:0 (1:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Pisa SC | ||||
| 1st(1st leg) | AS Roma | - | US Foggia | 1:0 (1:0) | ||
| 2nd (2nd leg) | US Foggia | - | AS Roma | 1:3 (1:2) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: AS Roma | ||||
| 1st(1st leg) | Giarre | - | Genoa CFC | 0:0 (0:0) | ||
| 2nd (2nd leg) | Genoa CFC | - | Giarre | 3:0 (2:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: Genoa CFC | ||||
| 1st(1st leg) | AS Bari | - | A.C.R. Messina | 0:0 (0:0) | ||
| 2nd (2nd leg) | A.C.R. Messina | - | AS Bari | 3:5 (0:0, 0:0, 0:0) pso | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: AS Bari | ||||
| 1st(1st leg) | Atalanta | - | Pescara Calcio | 2:0 (0:0) | ||
| 2nd (2nd leg) | Pescara Calcio | - | Atalanta | 1:0 (0:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 10/10/1990 | Winner: Atalanta | ||||
| 1st(1st leg) | US Lecce | - | Cagliari Calcio | 4:0 (0:0) | ||
| 2nd (2nd leg) | Cagliari Calcio | - | US Lecce | 0:1 (0:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: US Lecce | ||||
| 1st(1st leg) | AC Milan | - | US Triestina | 1:0 (1:0) | ||
| 2nd (2nd leg) | US Triestina | - | AC Milan | 1:1 (1:0) | ||
| 1st(1st leg): 05/09/1990 | 2nd (2nd leg): 12/09/1990 | Winner: AC Milan | ||||
