| Dates |
Season |
Cup |
Round |
Match |
Result |
| 20.09.2001 |
2001/02 |
UC |
First Round |
Chelsea FC - Levski Sofia |
3:0 (1:0) |
| 27.09.2001 |
2001/02 |
UC |
First Round |
Levski Sofia - Chelsea FC |
0:2 (0:2) |
| 27.09.2006 |
2006/07 |
CL |
Group stage |
Levski Sofia - Chelsea FC |
1:3 (0:1) |
| 05.12.2006 |
2006/07 |
CL |
Group stage |
Chelsea FC - Levski Sofia |
2:0 (1:0) |
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