| 3. Round | 24/08/2009 | Lokomotiv Plovdiv | - | Cherno More Varna | 1:0 | ||||
| 4. Round | 30/08/2009 | Cherno More Varna | - | Botev Plovdiv | 3:0 | ||||
| 5. Round | 13/09/2009 | PFC Beroe | - | Cherno More Varna | 0:0 | ||||
| 8. Round | 03/10/2009 | Cherno More Varna | - | PFC Litex Lovech | 0:0 | ||||
| 10. Round | 26/10/2009 | Cherno More Varna | - | Slavia Sofia | 1:1 | ||||
| 11. Round | 30/10/2009 | Pirin Blagoevgrad | - | Cherno More Varna | 1:0 | ||||
| 14. Round | 28/11/2009 | Cherno More Varna | - | CSKA Sofia | 0:0 |
Bulgaria