| 5. Round | 21/10/2023 | FC Crotone [Youth] | - | Pisa SC [Youth] | 0:3 | ||||
| 6. Round | 28/10/2023 | Pisa SC [Youth] | - | Benevento Calcio [Youth] | 1:1 | ||||
| 7. Round | 04/11/2023 | Ascoli Calcio [Youth] | - | Pisa SC [Youth] | 2:0 | ||||
| 8. Round | 11/11/2023 | Pisa SC [Youth] | - | Cosenza Calcio [Youth] | 1:0 | ||||
| 11. Round | 09/12/2023 | Virtus Entella [Youth] | - | Pisa SC [Youth] | 0:3 | ||||
| 12. Round | 16/12/2023 | Pisa SC [Youth] | - | Spezia Calcio [Youth] | 2:0 | ||||
| 15. Round | 20/01/2024 | SSC Napoli [Youth] | - | Pisa SC [Youth] | 0:0 |  |
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| 17. Round | 03/02/2024 | US Salernitana 1919 [Youth] | - | Pisa SC [Youth] | 1:0 | ||||
| 18. Round | 10/02/2024 | Pisa SC [Youth] | - | Virtus Entella [Youth] | 2:1 | ||||
| 29. Round | 04/05/2024 | AC Perugia Calcio [Youth] | - | Pisa SC [Youth] | 1:0 |
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