Head to Head
| Elite Club Friendlies | 2018/08/11 19:00 | Real Madrid v AC Milan | W | 3-1 |
| Elite Club Friendlies | 2015/07/30 12:00 | Real Madrid v AC Milan | W | 10-9 |
| Club Friendly List | 2014/12/30 16:00 | Real Madrid v AC Milan | L | 2-4 |
Home History
| Elite Club Friendlies | 2021/07/25 17:00 | Rangers v Real Madrid | L | 2-1 |
| Spain La Liga | 2021/05/22 16:00 | Real Madrid v Villarreal | W | 2-1 |
| Spain La Liga | 2021/05/16 16:30 | Athletic Bilbao v Real Madrid | W | 0-1 |
| Spain La Liga | 2021/05/13 20:00 | Granada v Real Madrid | W | 1-4 |
| Spain La Liga | 2021/05/09 19:00 | Real Madrid v Sevilla | D | 2-2 |
| UEFA Champions League | 2021/05/05 19:00 | Chelsea v Real Madrid | L | 2-0 |
| Spain La Liga | 2021/05/01 19:00 | Real Madrid v Osasuna | W | 2-0 |
| UEFA Champions League | 2021/04/27 19:00 | Real Madrid v Chelsea | D | 1-1 |
Away History
| Elite Club Friendlies | 2021/08/04 18:30 | Valencia v AC Milan | L | 5-3 |
| Elite Club Friendlies | 2021/07/31 18:30 | Nice v AC Milan | D | 1-1 |
| Elite Club Friendlies | 2021/07/24 15:00 | AC Milan v Modena | W | 5-0 |
| Italy Serie A | 2021/05/23 18:45 | Atalanta v AC Milan | W | 0-2 |
| Italy Serie A | 2021/05/16 18:45 | AC Milan v Cagliari | D | 0-0 |
| Italy Serie A | 2021/05/12 18:45 | Torino v AC Milan | W | 0-7 |
| Italy Serie A | 2021/05/09 18:45 | Juventus v AC Milan | W | 0-3 |
| Italy Serie A | 2021/05/01 18:45 | AC Milan v Benevento | W | 2-0 |