| 1. Round | 17/09/1939 | Torino FC | - | AC Milan | 2:1 | ||||
| 2. Round | 24/09/1939 | AC Milan | - | ACF Fiorentina | 3:1 | ||||
| 3. Round | 01/10/1939 | Genova 1893 Circolo del Calcio | - | AC Milan | 1:1 | ||||
| 9. Round | 19/11/1939 | AC Milan | - | AC Venezia | 2:1 | ||||
| 10. Round | 03/12/1939 | SSC Napoli | - | AC Milan | 1:4 |  |
|||
| 12. Round | 17/12/1939 | AS Ambrosiana-Inter | - | AC Milan | 0:3 | ||||
| 13. Round | 31/12/1939 | AC Milan | - | AS Roma | 3:0 | ||||
| 22. Round | 10/03/1940 | Bologna FC | - | AC Milan | 1:0 | ||||
| 23. Round | 17/03/1940 | AC Milan | - | Juventus | 1:2 |
Italy