| 3. Round | 04/10/1959 | AC Lanerossi Vicenza | - | AC Milan | 1:2 | ||||
| 4. Round | 11/10/1959 | AC Milan | - | SSC Napoli | 3:1 | ||||
| 7. Round | 08/11/1959 | Inter | - | AC Milan | 0:0 | ||||
| 9. Round | 22/11/1959 | AC Milan | - | AS Bari | 2:0 | ||||
| 11. Round | 13/12/1959 | AC Milan | - | US Palermo | 0:0 | ||||
| 13. Round | 27/12/1959 | Lazio Roma | - | AC Milan | 0:1 | ||||
| 12. Round | 01/01/1960 | AC Milan | - | Sampdoria | 4:0 | ||||
| 14. Round | 10/01/1960 | AC Milan | - | Juventus | 0:2 | ||||
| 15. Round | 17/01/1960 | Bologna FC | - | AC Milan | 0:3 | ||||
| 16. Round | 24/01/1960 | SPAL Ferrara | - | AC Milan | 0:3 | ||||
| 17. Round | 31/01/1960 | AC Milan | - | Atalanta | 2:1 | ||||
| 21. Round | 28/02/1960 | SSC Napoli | - | AC Milan | 1:1 | ||||
| 29. Round | 01/05/1960 | Sampdoria | - | AC Milan | 2:1 | ||||
| 34. Round | 05/06/1960 | Atalanta | - | AC Milan | 0:0 |
Italy