| 1. Round | 24/08/2019 | Virtus Entella | - | AS Livorno | 1:0 | ||||
| 2. Round | 31/08/2019 | AS Livorno | - | AC Perugia Calcio | 0:1 | ||||
| 4. Round | 21/09/2019 | AS Livorno | - | Pordenone Calcio | 2:1 | ||||
| 5. Round | 24/09/2019 | Cosenza Calcio | - | AS Livorno | 1:1 | ||||
| 8. Round | 21/10/2019 | Frosinone Calcio | - | AS Livorno | 1:0 |  |
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| 13. Round | 23/11/2019 | AS Livorno | - | Trapani Calcio | 1:2 |  |
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| 14. Round | 30/11/2019 | US Cremonese | - | AS Livorno | 0:0 | |
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| 16. Round | 14/12/2019 | AS Livorno | - | Benevento Calcio | 0:2 | ||||
| 17. Round | 21/12/2019 | FC Crotone | - | AS Livorno | 2:1 | ||||
| 18. Round | 26/12/2019 | AS Livorno | - | Delfino Pescara | 0:2 | ||||
| 29. Round | 20/06/2020 | AS Livorno | - | AS Cittadella | 0:2 | ||||
| 32. Round | 03/07/2020 | Trapani Calcio | - | AS Livorno | 2:1 | |
Italy