| 2. Round | 22/09/2019 | Chievo Verona [Youth] | - | Sampdoria [Youth] | 0:1 | ||||
| 5. Round | 19/10/2019 | Bologna FC [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 | ||||
| 17. Round | 03/02/2020 | Sampdoria [Youth] | - | Chievo Verona [Youth] | 2:2 | ||||
| 18. Round | 08/02/2020 | Sampdoria [Youth] | - | Delfino Pescara [Youth] | 1:0 | ||||
| 19. Round | 17/02/2020 | Lazio Roma [Youth] | - | Sampdoria [Youth] | 1:1 | ||||
| 20. Round | 22/02/2020 | Sampdoria [Youth] | - | Bologna FC [Youth] | 4:2 | ||||
| 22. Round | 08/03/2020 | Sampdoria [Youth] | - | Empoli FC [Youth] | 0:2 |
Italy