| 2. Round | 18/09/2021 | AC Monza [Youth] | - | Brescia Calcio [Youth] | 2:1 | ||||
| 4. Round | 02/10/2021 | AC Monza [Youth] | - | US Cremonese [Youth] | 3:2 |  |
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| 5. Round | 16/10/2021 | Como 1907 [Youth] | - | AC Monza [Youth] | 1:2 | ||||
| 6. Round | 23/10/2021 | AC Monza [Youth] | - | AC Reggiana 1919 [Youth] | 3:0 | ||||
| 7. Round | 30/10/2021 | Virtus Entella [Youth] | - | AC Monza [Youth] | 1:2 | |
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| 9. Round | 20/11/2021 | AC Monza [Youth] | - | US Alessandria 1912 [Youth] | 1:1 | ||||
| 10. Round | 27/11/2021 | L.R. Vicenza [Youth] | - | AC Monza [Youth] | 2:0 | ||||
| 11. Round | 04/12/2021 | AC Monza [Youth] | - | Parma Calcio 1913 [Youth] | 1:1 | |
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| 12. Round | 11/12/2021 | AC Monza [Youth] | - | Venezia FC [Youth] | 2:1 | ||||
| 14. Round | 29/01/2022 | AC Monza [Youth] | - | Pordenone Calcio [Youth] | 10:0 | |
Italy