| 2. Round | 10/09/2023 | SS Monopoli 1966 | - | Monterosi FC | 2:2 | ||||
| 3. Round | 17/09/2023 | Potenza | - | SS Monopoli 1966 | 2:1 | ||||
| 4. Round | 21/09/2023 | SS Monopoli 1966 | - | Calcio Catania | 0:0 |  |
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| 6. Round | 01/10/2023 | Juve Stabia | - | SS Monopoli 1966 | 1:0 | ||||
| 7. Round | 08/10/2023 | SS Monopoli 1966 | - | Foggia Calcio | 2:2 | ||||
| 8. Round | 15/10/2023 | Latina Calcio | - | SS Monopoli 1966 | 3:2 | |
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| 9. Round | 20/10/2023 | SS Monopoli 1966 | - | Virtus Francavilla | 3:0 | |
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| 10. Round | 25/10/2023 | SS Monopoli 1966 | - | AZ Picerno | 1:1 | ||||
| 13. Round | 12/11/2023 | FC Turris | - | SS Monopoli 1966 | 0:1 | ||||
| 14. Round | 19/11/2023 | SS Monopoli 1966 | - | Benevento Calcio | 3:0 | ||||
| 17. Round | 11/12/2023 | Taranto FC | - | SS Monopoli 1966 | 1:0 | |
Italy