| 2. Ronde | 10.09.2023 | SS Monopoli 1966 | - | Monterosi FC | 2:2 | ||||
| 3. Ronde | 17.09.2023 | Potenza | - | SS Monopoli 1966 | 2:1 | ||||
| 4. Ronde | 21.09.2023 | SS Monopoli 1966 | - | Calcio Catania | 0:0 |  |
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| 6. Ronde | 01.10.2023 | Juve Stabia | - | SS Monopoli 1966 | 1:0 | ||||
| 7. Ronde | 08.10.2023 | SS Monopoli 1966 | - | Foggia Calcio | 2:2 | ||||
| 8. Ronde | 15.10.2023 | Latina Calcio | - | SS Monopoli 1966 | 3:2 | |
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| 9. Ronde | 20.10.2023 | SS Monopoli 1966 | - | Virtus Francavilla | 3:0 | |
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| 10. Ronde | 25.10.2023 | SS Monopoli 1966 | - | AZ Picerno | 1:1 | ||||
| 13. Ronde | 12.11.2023 | FC Turris | - | SS Monopoli 1966 | 0:1 | ||||
| 14. Ronde | 19.11.2023 | SS Monopoli 1966 | - | Benevento Calcio | 3:0 | ||||
| 17. Ronde | 11.12.2023 | Taranto FC | - | SS Monopoli 1966 | 1:0 | |
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