| Dates |
Season |
Cup |
Round |
Match |
Result |
| 13.09.1959 |
1959/60 |
EC |
First Round |
Olympiacos Pireaus - AC Milan |
2:2 (2:1) |
| 23.09.1959 |
1959/60 |
EC |
First Round |
AC Milan - Olympiacos Pireaus |
3:1 (2:0) |
| 04.10.2018 |
2018/19 |
EL |
Group stage |
AC Milan - Olympiacos Pireaus |
3:1 (0:1) |
| 13.12.2018 |
2018/19 |
EL |
Group stage |
Olympiacos Pireaus - AC Milan |
3:1 (0:0) |
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