Chelsea have played A.C. Milan 4 times in competitive football, winning 2, drawing 2 and losing 0, first meeting on 15 Sep 1999 and most recently on 11 Oct 2022. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 15 Sep 1999 | 1999–00 | Champions League | H | A.C. Milan | 0–0 | 33,873 | |
| 26 Oct 1999 | 1999–00 | Champions League | A | A.C. Milan | 1–1 | Dennis Wise 77 | 74,855 |
| 5 Oct 2022 | 2022–23 | Champions League | H | A.C. Milan | 3–0 | Wesley Fofana 24, Pierre-Emerick Aubameyang 56, Reece James 62 | 39,537 |
| 11 Oct 2022 | 2022–23 | Champions League | A | A.C. Milan | 2–0 | Jorginho 21, Pierre-Emerick Aubameyang 34 | 75,051 |