| 2. Round | 02/09/2023 | Frosinone Calcio [Youth] | - | AC Monza [Youth] | 2:3 |  |
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| 3. Round | 17/09/2023 | AC Monza [Youth] | - | Torino FC [Youth] | 2:2 | ||||
| 5. Round | 30/09/2023 | US Lecce [Youth] | - | AC Monza [Youth] | 1:1 | ||||
| 9. Round | 05/11/2023 | Atalanta [Youth] | - | AC Monza [Youth] | 2:0 | ||||
| 10. Round | 10/11/2023 | AC Monza [Youth] | - | Sampdoria [Youth] | 2:0 | ||||
| 11. Round | 27/11/2023 | Sassuolo Calcio [Youth] | - | AC Monza [Youth] | 3:1 | ||||
| 12. Round | 04/12/2023 | Bologna FC [Youth] | - | AC Monza [Youth] | 4:3 | |
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| 28. Round | 08/04/2024 | AC Monza [Youth] | - | ACF Fiorentina [Youth] | 1:0 | ||||
| 30. Round | 21/04/2024 | AC Monza [Youth] | - | Lazio Roma [Youth] | 1:1 | ||||
| 34. Round | 17/05/2024 | AC Monza [Youth] | - | US Lecce [Youth] | 1:5 |
Italy