| 3. Ronde | 21.08.2009 | PFC Beroe | - | PSFC Chernomorets | 1:1 | ||||
| 6. Ronde | 19.09.2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 2:1 |  |
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| 7. Ronde | 27.09.2009 | Levski Sofia | - | PSFC Chernomorets | 0:1 | ||||
| 8. Ronde | 03.10.2009 | PSFC Chernomorets | - | PFC Montana | 1:1 |  |
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| 9. Ronde | 16.10.2009 | OFC Sliven | - | PSFC Chernomorets | 0:1 | ||||
| 10. Ronde | 24.10.2009 | PSFC Chernomorets | - | Botev Plovdiv | 2:0 | ||||
| 11. Ronde | 31.10.2009 | Minyor Pernik | - | PSFC Chernomorets | 2:0 | ||||
| 13. Ronde | 22.11.2009 | Slavia Sofia | - | PSFC Chernomorets | 3:2 | |
Bulgarije