| 1. Round | 17/09/1939 | Torino FC | - | AC Milan | 2:1 | ||||
| 7. Round | 29/10/1939 | AC Milan | - | Bologna FC | 0:2 | ||||
| 8. Round | 05/11/1939 | Juventus | - | AC Milan | 2:2 | ||||
| 9. Round | 19/11/1939 | AC Milan | - | AC Venezia | 2:1 | ||||
| 11. Round | 10/12/1939 | AC Milan | - | AC Liguria | 1:1 | ||||
| 18. Round | 04/02/1940 | AC Milan | - | Genova 1893 Circolo del Calcio | 2:2 | ||||
| 19. Round | 11/02/1940 | AS Bari | - | AC Milan | 2:0 |
Italy