| 1. Round | 18/09/1938 | AS Bari | - | US Livorno | 2:0 | ||||
| 2. Round | 25/09/1938 | US Livorno | - | Torino FC | 1:1 | ||||
| 13. Round | 08/01/1939 | US Livorno | - | SSC Napoli | 2:0 | ||||
| 14. Round | 15/01/1939 | AS Ambrosiana-Inter | - | US Livorno | 3:1 | ||||
| 15. Round | 22/01/1939 | US Livorno | - | Genova 1893 Circolo del Calcio | 2:2 | ||||
| 16. Round | 29/01/1939 | US Livorno | - | AS Bari | 3:0 | ||||
| 18. Round | 12/02/1939 | Bologna FC | - | US Livorno | 1:1 | ||||
| 19. Round | 19/02/1939 | US Livorno | - | Lazio Roma | 2:3 | ||||
| 20. Round | 26/02/1939 | Novara Calcio | - | US Livorno | 2:1 | ||||
| 21. Round | 05/03/1939 | US Livorno | - | AC Milan | 0:2 |
Italy