| 1. Round | 15/09/2019 | ACF Fiorentina [Youth] | - | Bologna FC [Youth] | 6:3 |  |
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| 3. Round | 28/09/2019 | ACF Fiorentina [Youth] | - | AS Roma [Youth] | 3:0 | |
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| 4. Round | 05/10/2019 | Torino FC [Youth] | - | ACF Fiorentina [Youth] | 1:1 | ||||
| 5. Round | 20/10/2019 | ACF Fiorentina [Youth] | - | Chievo Verona [Youth] | 1:1 |  |
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| 6. Round | 23/10/2019 | ACF Fiorentina [Youth] | - | Delfino Pescara [Youth] | 3:3 | |
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| 7. Round | 02/11/2019 | SSC Napoli [Youth] | - | ACF Fiorentina [Youth] | 1:1 | ||||
| 9. Round | 23/11/2019 | Empoli FC [Youth] | - | ACF Fiorentina [Youth] | 1:0 | ||||
| 10. Round | 30/11/2019 | ACF Fiorentina [Youth] | - | Atalanta [Youth] | 0:1 | ||||
| 13. Round | 21/12/2019 | Lazio Roma [Youth] | - | ACF Fiorentina [Youth] | 2:1 | ||||
| 15. Round | 18/01/2020 | Juventus [Youth] | - | ACF Fiorentina [Youth] | 2:1 | |
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| 16. Round | 25/01/2020 | Bologna FC [Youth] | - | ACF Fiorentina [Youth] | 0:1 | ||||
| 17. Round | 01/02/2020 | ACF Fiorentina [Youth] | - | Inter [Youth] | 1:2 | ||||
| 18. Round | 08/02/2020 | AS Roma [Youth] | - | ACF Fiorentina [Youth] | 2:1 | |
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| 19. Round | 15/02/2020 | ACF Fiorentina [Youth] | - | Torino FC [Youth] | 1:0 | |
Italy