| 7. Round | 23/01/2021 | Lazio Roma [Youth] | - | AC Milan [Youth] | 0:3 | ||||
| 9. Round | 09/02/2021 | Bologna FC [Youth] | - | AC Milan [Youth] | 3:0 | ||||
| 6. Round | 14/02/2021 | AC Milan [Youth] | - | Empoli FC [Youth] | 4:0 | ||||
| 11. Round | 21/02/2021 | Sampdoria [Youth] | - | AC Milan [Youth] | 1:0 |  |
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| 13. Round | 06/03/2021 | ACF Fiorentina [Youth] | - | AC Milan [Youth] | 3:1 | ||||
| 21. Round | 02/05/2021 | Empoli FC [Youth] | - | AC Milan [Youth] | 1:1 | ||||
| 27. Round | 05/06/2021 | Ascoli Calcio [Youth] | - | AC Milan [Youth] | 0:2 | ||||
| 28. Round | 09/06/2021 | AC Milan [Youth] | - | ACF Fiorentina [Youth] | 0:3 |
Italy