Head to Head
| UEFA Champions League | 2022/10/05 19:00 | Chelsea v Milan | L | 3-0 |
| Vänskapsmatcher - Elitklubbar | 2016/08/04 01:30 | Milan v Chelsea | L | 1-3 |
Home History
| Italien - Serie A | 2022/10/08 16:00 | Milan v Juventus | W | 2-0 |
| UEFA Champions League | 2022/10/05 19:00 | Chelsea v Milan | L | 3-0 |
| Italien - Serie A | 2022/10/01 18:45 | Empoli v Milan | W | 1-3 |
| Italien - Serie A | 2022/09/18 18:45 | Milan v Napoli | L | 1-2 |
| UEFA Champions League | 2022/09/14 16:45 | Milan v Dinamo Zagreb | W | 3-1 |
| Italien - Serie A | 2022/09/10 18:45 | Sampdoria v Milan | W | 1-2 |
| UEFA Champions League | 2022/09/06 19:00 | FC Salzburg v Milan | D | 1-1 |
| Italien - Serie A | 2022/09/03 16:00 | Milan v Inter | 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 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 |