| 1. Round | 26/08/2023 | AC Monza [Youth] | - | AC Milan [Youth] | 1:3 | ||||
| 10. Round | 10/11/2023 | AC Monza [Youth] | - | Sampdoria [Youth] | 2:0 |  |
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| 13. Round | 09/12/2023 | AC Monza [Youth] | - | Inter [Youth] | 1:1 | ||||
| 14. Round | 17/12/2023 | Lazio Roma [Youth] | - | AC Monza [Youth] | 1:1 | |
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| 15. Round | 23/12/2023 | AC Monza [Youth] | - | Juventus [Youth] | 3:3 | ||||
| 16. Round | 06/01/2024 | ACF Fiorentina [Youth] | - | AC Monza [Youth] | 2:2 | ||||
| 18. Round | 21/01/2024 | Cagliari Calcio [Youth] | - | AC Monza [Youth] | 1:2 | ||||
| 26. Round | 17/03/2024 | AC Monza [Youth] | - | Sassuolo Calcio [Youth] | 1:2 | ||||
| 27. Round | 01/04/2024 | Genoa CFC [Youth] | - | AC Monza [Youth] | 1:0 | ||||
| 28. Round | 08/04/2024 | AC Monza [Youth] | - | ACF Fiorentina [Youth] | 1:0 | ||||
| 29. Round | 13/04/2024 | Hellas Verona [Youth] | - | AC Monza [Youth] | 2:0 | ||||
| 30. Round | 21/04/2024 | AC Monza [Youth] | - | Lazio Roma [Youth] | 1:1 | ||||
| 31. Round | 27/04/2024 | AC Milan [Youth] | - | AC Monza [Youth] | 1:2 | ||||
| 32. Round | 04/05/2024 | AC Monza [Youth] | - | Frosinone Calcio [Youth] | 2:1 | ||||
| 34. Round | 17/05/2024 | AC Monza [Youth] | - | US Lecce [Youth] | 1:5 |
Italy