All countries
| 11. Round | Monza U20 | Fiorentina U20 | details | 21.11.2026 11:00 | |||
| 10. Round | Bologna U20 | Monza U20 | 3:0 (3:0, 0:0) | details | 07.11.2026 | |||
| 9. Round | Monza U20 | AC Milan U20 | 0:5 (0:2, 0:3) | details | 31.10.2026 | |||
| 1/32-finals | Monza U20 | Brescia U19 | 5:1 (2:0, 3:1) | details | 27.10.2026 | |||
| 8. Round | Cesena U20 | Monza U20 | 2:2 (0:1, 2:1) | details | 24.10.2026 | |||
| 7. Round | Monza U20 | Juventus U20 | 1:2 (0:2, 1:0) | details | 18.10.2026 | |||
| 11. Round | Monza U20 | Fiorentina U20 | details | 21.11.2026 11:00 | |||
| 12. Round | Atalanta U20 | Monza U20 | details | 27.11.2026 17:00 | |||
| 1/16-finals | Monza U20 | Entella U19 | details | 01.12.2026 14:00 | |||
| 13. Round | Monza U20 | Parma U20 | details | 05.12.2026 15:00 | |||
| 14. Round | Albinoleffe U20 | Monza U20 | details | 11.12.2026 14:00 | |||