| 6. Round | 25/09/2019 | AC Rimini | - | AS Gubbio | 1:1 | ||||
| 7. Round | 29/09/2019 | AS Gubbio | - | Feralpisalò | 0:0 | ||||
| 8. Round | 06/10/2019 | Reggio Audace FC | - | AS Gubbio | 1:1 |  |
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| 9. Round | 13/10/2019 | AS Gubbio | - | Carpi FC | 1:2 | ||||
| 10. Round | 19/10/2019 | FC Südtirol | - | AS Gubbio | 3:0 | ||||
| 14. Round | 10/11/2019 | Piacenza Calcio | - | AS Gubbio | 1:0 | ||||
| 16. Round | 24/11/2019 | Ravenna Calcio | - | AS Gubbio | 3:3 | |
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| 18. Round | 09/12/2019 | Sambenedettese | - | AS Gubbio | 2:0 | |
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| 22. Round | 19/01/2020 | AS Gubbio | - | Arzignano Valchiampo | 0:1 | ||||
| 20. Round | 23/01/2020 | AS Gubbio | - | US Triestina | 2:0 | ||||
| 23. Round | 26/01/2020 | Alma Juventus Fano | - | AS Gubbio | 0:2 | ||||
| 26. Round | 16/02/2020 | Feralpisalò | - | AS Gubbio | 3:3 | ||||
| 27. Round | 23/02/2020 | AS Gubbio | - | Reggio Audace FC | 0:0 | |
Italy