| 2. Round | 23/09/2023 | SS Monopoli 1966 [Youth] | - | Delfino Pescara [Youth] | 3:2 | ||||
| 3. Round | 30/09/2023 | FC Crotone [Youth] | - | SS Monopoli 1966 [Youth] | 4:3 | ||||
| 4. Round | 07/10/2023 | SS Monopoli 1966 [Youth] | - | AC Perugia Calcio [Youth] | 1:3 | ||||
| 5. Round | 21/10/2023 | Spezia Calcio [Youth] | - | SS Monopoli 1966 [Youth] | 3:0 | ||||
| 6. Round | 28/10/2023 | SS Monopoli 1966 [Youth] | - | Palermo FC [Youth] | 0:1 |  |
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| 7. Round | 04/11/2023 | Cesena FC [Youth] | - | SS Monopoli 1966 [Youth] | 8:0 | ||||
| 9. Round | 26/11/2023 | SS Monopoli 1966 [Youth] | - | Pisa SC [Youth] | 3:2 |
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