| 1. Round | 07/08/2009 | PFC Beroe | - | Lokomotiv Sofia | 2:1 | ||||
| 2. Round | 14/08/2009 | Lokomotiv Sofia | - | FK Sportist Svoge | 3:2 | ||||
| 3. Round | 23/08/2009 | Lokomotiv 2012 Mezdra | - | Lokomotiv Sofia | 1:2 | ||||
| 4. Round | 29/08/2009 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 1:0 | ||||
| 5. Round | 12/09/2009 | Levski Sofia | - | Lokomotiv Sofia | 1:2 | ||||
| 6. Round | 18/09/2009 | Lokomotiv Sofia | - | PFC Montana | 0:0 | ||||
| 8. Round | 03/10/2009 | Lokomotiv Sofia | - | Botev Plovdiv | 2:2 | ||||
| 10. Round | 24/10/2009 | Lokomotiv Sofia | - | PFC Litex Lovech | 0:1 |  |
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| 11. Round | 01/11/2009 | Slavia Sofia | - | Lokomotiv Sofia | 0:0 | ||||
| 12. Round | 07/11/2009 | Cherno More Varna | - | Lokomotiv Sofia | 4:2 | ||||
| 13. Round | 21/11/2009 | Lokomotiv Sofia | - | CSKA Sofia | 2:2 | ||||
| 14. Round | 29/11/2009 | PSFC Chernomorets | - | Lokomotiv Sofia | 0:2 |  |
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| 15. Round | 05/12/2009 | Lokomotiv Sofia | - | Lokomotiv Plovdiv | 3:0 |
North Macedonia