| 1. Ronde | 01.09.2023 | AS Gubbio | - | ASD Pineto Calcio | 1:1 | ||||
| 2. Ronde | 09.09.2023 | Ancona 1905 | - | AS Gubbio | 1:2 |  |
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| 3. Ronde | 16.09.2023 | AS Gubbio | - | Fermana FC | 0:0 | ||||
| 4. Ronde | 19.09.2023 | Lucchese | - | AS Gubbio | 0:0 | ||||
| 5. Ronde | 23.09.2023 | AS Gubbio | - | Vis Pesaro | 1:0 | ||||
| 6. Ronde | 02.10.2023 | Delfino Pescara | - | AS Gubbio | 3:2 | |
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| 7. Ronde | 09.10.2023 | AS Gubbio | - | Carrarese Calcio | 2:0 | |
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| 9. Ronde | 22.10.2023 | AS Gubbio | - | Olbia Calcio | 1:0 |  |
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| 10. Ronde | 25.10.2023 | AS Gubbio | - | Juventus II | 1:1 | ||||
| 11. Ronde | 30.10.2023 | US Arezzo | - | AS Gubbio | 1:0 | ||||
| 12. Ronde | 05.11.2023 | AS Gubbio | - | Cesena FC | 1:1 | |
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| 13. Ronde | 12.11.2023 | AC Perugia Calcio | - | AS Gubbio | 1:0 | ||||
| 14. Ronde | 19.11.2023 | AS Gubbio | - | USD Sestri Levante | 5:2 | ||||
| 16. Ronde | 02.12.2023 | AS Gubbio | - | SPAL 2013 Ferrara | 0:0 | ||||
| 17. Ronde | 09.12.2023 | US Pontedera | - | AS Gubbio | 2:1 | ||||
| 19. Ronde | 22.12.2023 | AC Rimini | - | AS Gubbio | 1:2 | ||||
| 20. Ronde | 07.01.2024 | ASD Pineto Calcio | - | AS Gubbio | 1:2 | |
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| 21. Ronde | 14.01.2024 | AS Gubbio | - | Ancona 1905 | 0:0 |
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