Milan U20: every transfer in and out, fees paid and earned, squad market value, €6.9m spent and €8.5m earned.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-08-11 | Fredrik Nissen | Milan U20 | AIK | — |
| 2025-07-24 | Dorian Paloschi | Milan U20 | Grasshoppers | Free |
| 2025-07-01 | Matteo Duțu | Milan U20 | Milan Futuro | — |
| 2025-07-01 | Mateusz Skoczylas | Milan U20 | Milan Futuro | — |
| 2025-07-01 | Demirel Hodzic | Milan U20 | Milan Futuro | — |
| 2024-08-23 | Demirel Hodzic | Bologna U20 | Milan U20 | €500k |
| 2024-07-12 | Matteo Duțu | Lazio U20 | Milan U20 | €500k |
| 2024-07-12 | Andrea Bartoccioni | Milan U19 | Renate | — |
| 2024-07-01 | Victor Eletu | Milan U19 | Milan U23 | — |
| 2024-07-01 | Noah Raveyre | Milan U19 | Milan U23 | — |
| 2024-07-01 | Lorenzo Torriani | Milan U20 | AC Milan | — |
| 2024-07-01 | Kevin Zeroli | Milan U19 | Milan U23 | — |
| 2024-07-01 | Jan-Carlo Simić | Milan U20 | AC Milan | — |
| 2024-07-01 | Francesco Camarda | Milan U20 | Milan Futuro | — |
| 2024-07-01 | Davide Bartesaghi | Milan U20 | Milan Futuro | — |
| 2024-07-01 | Clinton Nsiala | Milan U20 | Rangers | Free |
| 2024-07-01 | Andrei Coubiș | Milan U20 | Milan Futuro | — |
| 2024-01-09 | Bob Murphy Omoregbe | Milan U19 | Sestri Levante | Free |
| 2023-08-30 | Fredrik Nissen | Brommapojkarna | Milan U19 | €500k |
| 2023-08-26 | Alexander Simmelhack | Copenhagen U19 | Milan U19 | Loan |