| 1. Round | 14/09/2019 | Sampdoria [Youth] | - | Atalanta [Youth] | 2:3 | ||||
| 2. Round | 22/09/2019 | Chievo Verona [Youth] | - | Sampdoria [Youth] | 0:1 | ||||
| 3. Round | 29/09/2019 | Delfino Pescara [Youth] | - | Sampdoria [Youth] | 3:0 | ||||
| 4. Round | 04/10/2019 | Sampdoria [Youth] | - | Lazio Roma [Youth] | 2:1 | ||||
| 5. Round | 19/10/2019 | Bologna FC [Youth] | - | Sampdoria [Youth] | 2:0 | ||||
| 6. Round | 28/10/2019 | Sampdoria [Youth] | - | Torino FC [Youth] | 3:0 | ||||
| 7. Round | 03/11/2019 | Empoli FC [Youth] | - | Sampdoria [Youth] | 1:0 | ||||
| 10. Round | 30/11/2019 | Sampdoria [Youth] | - | Juventus [Youth] | 0:2 | ||||
| 11. Round | 08/12/2019 | Cagliari Calcio [Youth] | - | Sampdoria [Youth] | 2:0 | ||||
| 12. Round | 13/12/2019 | Sampdoria [Youth] | - | Genoa CFC [Youth] | 1:0 | ||||
| 13. Round | 22/12/2019 | Sampdoria [Youth] | - | SSC Napoli [Youth] | 2:1 | ||||
| 14. Round | 11/01/2020 | ACF Fiorentina [Youth] | - | Sampdoria [Youth] | 2:2 | ||||
| 15. Round | 18/01/2020 | Sampdoria [Youth] | - | AS Roma [Youth] | 5:4 |  |
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| 8. Round | 22/01/2020 | Sampdoria [Youth] | - | Inter [Youth] | 2:1 | ||||
| 16. Round | 25/01/2020 | Atalanta [Youth] | - | Sampdoria [Youth] | 2:2 |
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