| 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 | ||||
| 9. Round | 23/11/2019 | Sassuolo Calcio [Youth] | - | Sampdoria [Youth] | 5:1 | ||||
| 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 |  |
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| 22. Round | 08/03/2020 | Sampdoria [Youth] | - | Empoli FC [Youth] | 0:2 |
Italy