| 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 | ||||
| 4. Round | 08/10/1939 | AC Milan | - | AS Bari | 4:0 | ||||
| 5. Round | 15/10/1939 | AC Milan | - | Lazio Roma | 0:2 | ||||
| 10. Round | 03/12/1939 | SSC Napoli | - | AC Milan | 1:4 | ||||
| 11. Round | 10/12/1939 | AC Milan | - | AC Liguria | 1:1 | ||||
| 12. Round | 17/12/1939 | AS Ambrosiana-Inter | - | AC Milan | 0:3 | ||||
| 13. Round | 31/12/1939 | AC Milan | - | AS Roma | 3:0 |  |
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| 14. Round | 07/01/1940 | US Triestina | - | AC Milan | 1:1 | ||||
| 15. Round | 15/01/1940 | AC Milan | - | Modena FC | 4:0 | ||||
| 17. Round | 28/01/1940 | ACF Fiorentina | - | AC Milan | 1:0 | ||||
| 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 | ||||
| 30. Round | 02/06/1940 | Modena FC | - | AC Milan | 2:2 |
Italy