| 2. Spieltag | 09.09.2023 | Ancona 1905 | - | AS Gubbio | 1:2 | ||||
| 4. Spieltag | 19.09.2023 | Lucchese | - | AS Gubbio | 0:0 |  |
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| 5. Spieltag | 23.09.2023 | AS Gubbio | - | Vis Pesaro | 1:0 | ||||
| 6. Spieltag | 02.10.2023 | Delfino Pescara | - | AS Gubbio | 3:2 | ||||
| 7. Spieltag | 09.10.2023 | AS Gubbio | - | Carrarese Calcio | 2:0 | ||||
| 8. Spieltag | 15.10.2023 | Virtus Entella | - | AS Gubbio | 2:1 | ||||
| 9. Spieltag | 22.10.2023 | AS Gubbio | - | Olbia Calcio | 1:0 | ||||
| 10. Spieltag | 25.10.2023 | AS Gubbio | - | Juventus II | 1:1 | ||||
| 11. Spieltag | 30.10.2023 | US Arezzo | - | AS Gubbio | 1:0 |  |
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| 13. Spieltag | 12.11.2023 | AC Perugia Calcio | - | AS Gubbio | 1:0 | ||||
| 14. Spieltag | 19.11.2023 | AS Gubbio | - | USD Sestri Levante | 5:2 | ||||
| 15. Spieltag | 26.11.2023 | SEF Torres 1903 | - | AS Gubbio | 3:1 | |
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| 18. Spieltag | 10.01.2024 | AS Gubbio | - | US Recanatese | 3:1 |
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