| 1. Round | 10/09/2022 | AC Monza [Youth] | - | US Alessandria 1912 [Youth] | 5:2 |  |
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| 2. Round | 17/09/2022 | Calcio Padova [Youth] | - | AC Monza [Youth] | 1:4 | ||||
| 3. Round | 01/10/2022 | AC Monza [Youth] | - | L.R. Vicenza [Youth] | 1:1 | ||||
| 7. Round | 29/10/2022 | AC Monza [Youth] | - | Parma Calcio 1913 [Youth] | 0:2 | ||||
| 9. Round | 12/11/2022 | Brescia Calcio [Youth] | - | AC Monza [Youth] | 2:7 | |
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| 10. Round | 26/11/2022 | AC Monza [Youth] | - | US Cremonese [Youth] | 1:0 | ||||
| 11. Round | 03/12/2022 | AC Monza [Youth] | - | Como 1907 [Youth] | 0:3 | ||||
| 12. Round | 10/12/2022 | Genoa CFC [Youth] | - | AC Monza [Youth] | 1:0 | ||||
| 14. Round | 14/01/2023 | AC Reggiana 1919 [Youth] | - | AC Monza [Youth] | 1:3 | ||||
| 15. Round | 21/01/2023 | AC Monza [Youth] | - | Feralpisalò [Youth] | 3:1 | |
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| 16. Round | 28/01/2023 | US Alessandria 1912 [Youth] | - | AC Monza [Youth] | 1:1 |
Italy