Head-to-head
Competition type
Aggregate 9 matches
ENG
5
wins
3 draws
ITA
1
wins
Goals 17 – 6
All meetings
Date Home Score Away R Tournament
☆ 08 Aug 2026 Chelsea 3–0 AC Milan H ITL · Club Friendlies
☆ 10 Aug 2025 Chelsea 4–1 AC Milan H ITL · Club Friendlies
☆ 11 Oct 2022 AC Milan 0–2 Chelsea A ITL · UEFA Champions League Group stage
☆ 05 Oct 2022 Chelsea 3–0 AC Milan H ITL · UEFA Champions League Group stage
☆ 26 Oct 1999 AC Milan 1–1 Chelsea D ITL · UEFA Champions League Group stage
☆ 15 Sep 1999 Chelsea 0–0 AC Milan D ITL · UEFA Champions League Group stage
☆ 23 Sep 1965 AC Milan 1–1 Chelsea D ITL · Inter-Cities Fairs Cup
☆ 09 Sep 1965 Chelsea 2–1 AC Milan H ITL · Inter-Cities Fairs Cup
☆ 25 Aug 1965 AC Milan 2–1 Chelsea H ITL · Inter-Cities Fairs Cup