| 1. Round | 01/09/2023 | AC Rimini | - | US Arezzo | 1:2 | ||||
| 2. Round | 09/09/2023 | US Arezzo | - | Carrarese Calcio | 1:3 | ||||
| 3. Round | 16/09/2023 | Delfino Pescara | - | US Arezzo | 3:2 | ||||
| 4. Round | 19/09/2023 | US Arezzo | - | Olbia Calcio | 1:1 | ||||
| 9. Round | 23/10/2023 | US Arezzo | - | SPAL 2013 Ferrara | 3:1 | ||||
| 10. Round | 26/10/2023 | Ancona 1905 | - | US Arezzo | 3:0 | ||||
| 11. Round | 30/10/2023 | US Arezzo | - | AS Gubbio | 1:0 |  |
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| 12. Round | 05/11/2023 | Vis Pesaro | - | US Arezzo | 1:1 |
Czech Republic