| 1. Jornada | 24.08.2019 | Virtus Entella | - | AS Livorno | 1:0 | ||||
| 2. Jornada | 31.08.2019 | AS Livorno | - | AC Perugia Calcio | 0:1 | ||||
| 3. Jornada | 14.09.2019 | Ascoli Calcio | - | AS Livorno | 2:0 |  |
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| 4. Jornada | 21.09.2019 | AS Livorno | - | Pordenone Calcio | 2:1 | ||||
| 7. Jornada | 05.10.2019 | AS Livorno | - | Chievo | 3:4 | ||||
| 8. Jornada | 21.10.2019 | Frosinone | - | AS Livorno | 1:0 | ||||
| 10. Jornada | 29.10.2019 | AS Cittadella | - | AS Livorno | 1:0 | ||||
| 16. Jornada | 14.12.2019 | AS Livorno | - | Benevento Calcio | 0:2 | |
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| 17. Jornada | 21.12.2019 | FC Crotone | - | AS Livorno | 2:1 | |
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| 18. Jornada | 26.12.2019 | AS Livorno | - | Delfino Pescara | 0:2 | ||||
| 25. Jornada | 23.02.2020 | US Salernitana 1919 | - | AS Livorno | 1:0 |
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