Head to Head
| Italy Campionato Primavera 1 | 2023/09/02 09:00 | AC Milan U19 v Bologna U19 | L | 4-1 |
| Italy Campionato Primavera 1 | 2023/03/10 15:00 | AC Milan U19 v Bologna U19 | L | 1-0 |
| Italy Campionato Primavera 1 | 2022/10/02 09:00 | Bologna U19 v AC Milan U19 | L | 0-3 |
| Italy Campionato Primavera 1 | 2022/04/23 13:00 | AC Milan U19 v Bologna U19 | W | 1-4 |
| Italy Campionato Primavera 1 | 2022/02/09 14:00 | Bologna U19 v AC Milan U19 | L | 2-5 |
| Italy Campionato Primavera 1 | 2021/05/22 15:00 | AC Milan U19 v Bologna U19 | L | 4-2 |
| Italy Campionato Primavera 1 | 2021/02/09 14:00 | Bologna U19 v AC Milan U19 | W | 3-0 |
| Italy Campionato Primavera 1 | 2018/02/03 12:00 | AC Milan U19 v Bologna U19 | D | 0-0 |
Home History
| Italy Campionato Primavera 1 | 2024/04/27 13:00 | Sassuolo U19 v Bologna U19 | L | 3-2 |
| Italy Campionato Primavera 1 | 2024/04/14 13:00 | Sampdoria U19 v Bologna U19 | W | 1-2 |
| Italy Campionato Primavera 1 | 2024/04/06 09:00 | Bologna U19 v Juventus U19 | W | 3-0 |
| Italy Campionato Primavera 1 | 2024/03/30 14:00 | Frosinone U19 v Bologna U19 | D | 0-0 |
| Italy Campionato Primavera 1 | 2024/03/17 14:00 | Bologna U19 v Empoli U19 | L | 0-1 |
| Italy Campionato Primavera 1 | 2024/03/11 14:00 | Lazio U19 v Bologna U19 | L | 3-0 |
| Italy Campionato Primavera 1 | 2024/03/02 14:00 | Bologna U19 v Hellas Verona U19 | D | 2-2 |
| Italy Campionato Primavera 1 | 2024/02/26 13:00 | Fiorentina U19 v Bologna U19 | L | 5-0 |
Away History
| Italy Campionato Primavera 1 | 2024/04/27 11:00 | AC Milan U19 v Monza U19 | L | 1-2 |
| UEFA Youth League | 2024/04/22 16:00 | Olympiakos U19 v AC Milan U19 | L | 3-0 |
| UEFA Youth League | 2024/04/19 16:00 | FC Porto U19 v AC Milan U19 | W | 5-6 |
| Italy Campionato Primavera 1 | 2024/04/13 09:00 | AC Milan U19 v Empoli U19 | W | 3-2 |
| Italy Campionato Primavera 1 | 2024/04/08 16:30 | Sampdoria U19 v AC Milan U19 | L | 2-0 |
| Italy Campionato Primavera 1 | 2024/04/01 09:00 | Juventus U19 v AC Milan U19 | W | 0-1 |
| Italy Campionato Primavera 1 | 2024/03/17 09:45 | AC Milan U19 v Lazio U19 | W | 2-0 |
| UEFA Youth League | 2024/03/13 15:00 | AC Milan U19 v Real Madrid U19 | W | 5-4 |
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