| Dates |
Season |
Cup |
Round |
Match |
Result |
| 09.02.1966 |
1965/66 |
ICF |
1/8 Final |
AC Milan - Chelsea FC |
2:1 (0:0) |
| 16.02.1966 |
1965/66 |
ICF |
1/8 Final |
Chelsea FC - AC Milan |
2:1 (2:1) |
| 02.03.1966 |
1965/66 |
ICF |
1/8 Final |
AC Milan - Chelsea FC |
1:1 (0:1) |
| 15.09.1999 |
1999/00 |
CL |
Group stage 1 |
Chelsea FC - AC Milan |
0:0 (0:0) |
| 26.10.1999 |
1999/00 |
CL |
Group stage 1 |
AC Milan - Chelsea FC |
1:1 (0:0) |
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