| 16. Round | 06/01/2024 | ACF Fiorentina [Youth] | - | AC Monza [Youth] | 2:2 | ||||
| 17. Round | 13/01/2024 | AC Monza [Youth] | - | Hellas Verona [Youth] | 2:3 | ||||
| 18. Round | 21/01/2024 | Cagliari Calcio [Youth] | - | AC Monza [Youth] | 1:2 | ||||
| 19. Round | 26/01/2024 | AC Monza [Youth] | - | Atalanta [Youth] | 2:2 | ||||
| 20. Round | 04/02/2024 | AS Roma [Youth] | - | AC Monza [Youth] | 1:4 |  |
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| 21. Round | 10/02/2024 | AC Monza [Youth] | - | Bologna FC [Youth] | 2:2 | |
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| 25. Round | 10/03/2024 | Torino FC [Youth] | - | AC Monza [Youth] | 4:0 | ||||
| 27. Round | 01/04/2024 | Genoa CFC [Youth] | - | AC Monza [Youth] | 1:0 | |
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| 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 | |
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| 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 |  |
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Italy