| 1. Round | 10/09/2022 | SS Monopoli 1966 [Youth] | - | FC Crotone [Youth] | 0:2 |  |
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| 2. Round | 17/09/2022 | Lazio Roma [Youth] | - | SS Monopoli 1966 [Youth] | 5:0 | ||||
| 3. Round | 01/10/2022 | SS Monopoli 1966 [Youth] | - | Spezia Calcio [Youth] | 1:3 | |
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| 4. Round | 08/10/2022 | Delfino Pescara [Youth] | - | SS Monopoli 1966 [Youth] | 2:1 | ||||
| 5. Round | 15/10/2022 | SS Monopoli 1966 [Youth] | - | AC Perugia Calcio [Youth] | 1:0 |  |
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| 6. Round | 22/10/2022 | Cosenza Calcio [Youth] | - | SS Monopoli 1966 [Youth] | 1:2 | |
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| 7. Round | 29/10/2022 | SS Monopoli 1966 [Youth] | - | Viterbese [Youth] | 1:2 | ||||
| 8. Round | 05/11/2022 | US Salernitana 1919 [Youth] | - | SS Monopoli 1966 [Youth] | 1:2 | |
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| 9. Round | 12/11/2022 | SS Monopoli 1966 [Youth] | - | Imolese Calcio [Youth] | 3:1 | ||||
| 13. Round | 17/12/2022 | Ternana Calcio [Youth] | - | SS Monopoli 1966 [Youth] | 4:0 |
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