| 1. Round | 26/08/1989 | AC Cesena | - | AC Milan | 0:3 |  |
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| 3. Round | 05/09/1989 | Atalanta | - | AC Milan | 0:1 | ||||
| 4. Round | 09/09/1989 | AC Milan | - | Udinese Calcio | 3:1 | ||||
| 5. Round | 16/09/1989 | Genoa CFC | - | AC Milan | 1:1 | ||||
| 6. Round | 23/09/1989 | AC Milan | - | ACF Fiorentina | 1:1 | ||||
| 7. Round | 01/10/1989 | SSC Napoli | - | AC Milan | 3:0 | ||||
| 8. Round | 08/10/1989 | US Cremonese | - | AC Milan | 1:0 | ||||
| 9. Round | 22/10/1989 | AC Milan | - | AS Roma | 1:0 | ||||
| 10. Round | 29/10/1989 | Ascoli Calcio | - | AC Milan | 1:0 | ||||
| 13. Round | 25/11/1989 | AC Milan | - | US Lecce | 2:0 | ||||
| 14. Round | 02/12/1989 | AC Milan | - | Bologna FC | 1:0 | ||||
| 21. Round | 20/01/1990 | Udinese Calcio | - | AC Milan | 0:2 | ||||
| 26. Round | 24/02/1990 | AS Roma | - | AC Milan | 0:4 | ||||
| 27. Round | 03/03/1990 | AC Milan | - | Ascoli Calcio | 2:1 | |
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| 28. Round | 10/03/1990 | Juventus | - | AC Milan | 3:0 | ||||
| 30. Round | 24/03/1990 | US Lecce | - | AC Milan | 1:2 | ||||
| 31. Round | 07/04/1990 | Bologna FC | - | AC Milan | 0:0 |
Italy
