| Dates |
Season |
Cup |
Round |
Match |
Result |
| 20.09.1967 |
1967/68 |
CWC |
1/16 Final |
AC Milan - Levski Sofia |
5:1 (0:0) |
| 11.10.1967 |
1967/68 |
CWC |
1/16 Final |
Levski Sofia - AC Milan |
1:1 (0:1) |
| 18.10.1978 |
1978/79 |
UC |
1/16 Final |
Levski-Spartak Sofia - AC Milan |
1:1 (1:1) |
| 01.11.1978 |
1978/79 |
UC |
1/16 Final |
AC Milan - Levski-Spartak Sofia |
3:0 (2:0) |
| 07.09.1988 |
1988/89 |
EC |
First Round |
Vitosha Sofia - AC Milan |
0:2 (0:1) |
| 05.10.1988 |
1988/89 |
EC |
First Round |
AC Milan - Vitosha Sofia |
5:2 (3:1) |
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