| 6. Round | 22/10/2022 | SPAL 2013 Ferrara [Youth] | - | AC Monza [Youth] | 0:1 |  |
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| 8. Round | 05/11/2022 | Venezia FC [Youth] | - | AC Monza [Youth] | 2:3 | ||||
| 9. Round | 12/11/2022 | Brescia Calcio [Youth] | - | AC Monza [Youth] | 2:7 | ||||
| 13. Round | 17/12/2022 | AC Monza [Youth] | - | AS Cittadella [Youth] | 6:0 | ||||
| 15. Round | 21/01/2023 | AC Monza [Youth] | - | Feralpisalò [Youth] | 3:1 | ||||
| 22. Round | 11/03/2023 | Parma Calcio 1913 [Youth] | - | AC Monza [Youth] | 1:2 | ||||
| 25. Round | 08/04/2023 | US Cremonese [Youth] | - | AC Monza [Youth] | 2:2 | ||||
| 26. Round | 15/04/2023 | Como 1907 [Youth] | - | AC Monza [Youth] | 2:3 | ||||
| 27. Round | 22/04/2023 | AC Monza [Youth] | - | Genoa CFC [Youth] | 0:2 | |
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| 28. Round | 29/04/2023 | AS Cittadella [Youth] | - | AC Monza [Youth] | 0:1 |  |
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| 30. Round | 13/05/2023 | Feralpisalò [Youth] | - | AC Monza [Youth] | 0:1 |
Italy