All countries
| 11. Round | Lazio U20 | AC Milan U20 | details | 22.11.2026 11:00 | |||
| 10. Round | AC Milan U20 | Albinoleffe U20 | 5:1 (3:1, 2:0) | details | 08.11.2026 | |||
| 9. Round | Monza U20 | AC Milan U20 | 0:5 (0:2, 0:3) | details | 31.10.2026 | |||
| 1/32-finals | AC Milan U20 | Catanzaro U19 | 2:1 (1:0, 1:1) | details | 28.10.2026 | |||
| 8. Round | Fiorentina U20 | AC Milan U20 | 4:2 (1:0, 3:2) | details | 24.10.2026 | |||
| 7. Round | AC Milan U20 | Cagliari U20 | 2:0 (1:0, 1:0) | details | 17.10.2026 | |||
| 11. Round | Lazio U20 | AC Milan U20 | details | 22.11.2026 11:00 | |||
| 12. Round | AC Milan U20 | Lecce U20 | details | 28.11.2026 11:00 | |||
| 1/16-finals | AC Milan U20 | Como U20 | details | 02.12.2026 14:30 | |||
| 13. Round | AC Milan U20 | Genoa U20 | details | 06.12.2026 11:00 | |||