| 3. Round | 05/09/1989 | Atalanta | - | AC Milan | 0:1 | ||||
| 8. Round | 08/10/1989 | US Cremonese | - | AC Milan | 1:0 |  |
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| 9. Round | 22/10/1989 | AC Milan | - | AS Roma | 1:0 | ||||
| 11. Round | 04/11/1989 | AC Milan | - | Juventus | 3:2 | ||||
| 13. Round | 25/11/1989 | AC Milan | - | US Lecce | 2:0 | |
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| 14. Round | 02/12/1989 | AC Milan | - | Bologna FC | 1:0 | ||||
| 27. Round | 03/03/1990 | AC Milan | - | Ascoli Calcio | 2:1 | ||||
| 30. Round | 24/03/1990 | US Lecce | - | AC Milan | 1:2 | ||||
| 32. Round | 13/04/1990 | AC Milan | - | Sampdoria | 1:0 | ||||
| 34. Round | 28/04/1990 | AC Milan | - | AS Bari | 4:0 |
Italy