Head to Head
| UEFA Champions League | 2022/10/05 19:00 | Chelsea v AC Milan | L | 3-0 |
| Elite Club Friendlies | 2016/08/04 01:30 | AC Milan v Chelsea | L | 1-3 |
Home History
| Italy Serie A | 2022/10/08 16:00 | AC Milan v Juventus | W | 2-0 |
| UEFA Champions League | 2022/10/05 19:00 | Chelsea v AC Milan | L | 3-0 |
| Italy Serie A | 2022/10/01 18:45 | Empoli v AC Milan | W | 1-3 |
| Italy Serie A | 2022/09/18 18:45 | AC Milan v Napoli | L | 1-2 |
| UEFA Champions League | 2022/09/14 16:45 | AC Milan v Dinamo Zagreb | W | 3-1 |
| Italy Serie A | 2022/09/10 18:45 | Sampdoria v AC Milan | W | 1-2 |
| UEFA Champions League | 2022/09/06 19:00 | FC Salzburg v AC Milan | D | 1-1 |
| Italy Serie A | 2022/09/03 16:00 | AC Milan v Inter Milan | W | 3-2 |
Away History
| England Premier League | 2022/10/08 14:00 | Chelsea v Wolverhampton | W | 3-0 |
| UEFA Champions League | 2022/10/05 19:00 | Chelsea v AC Milan | W | 3-0 |
| England Premier League | 2022/10/01 14:00 | Crystal Palace v Chelsea | W | 1-2 |
| UEFA Champions League | 2022/09/14 19:00 | Chelsea v FC Salzburg | D | 1-1 |
| UEFA Champions League | 2022/09/06 16:45 | Dinamo Zagreb v Chelsea | L | 1-0 |
| England Premier League | 2022/09/03 14:00 | Chelsea v West Ham | W | 2-1 |
| England Premier League | 2022/08/30 18:45 | Southampton v Chelsea | L | 2-1 |
| England Premier League | 2022/08/27 14:00 | Chelsea v Leicester | W | 2-1 |