| 2. Round | 16/08/2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 | ||||
| 10. Round | 26/10/2008 | Lokomotiv Plovdiv | - | PFC Litex Lovech | 1:3 | ||||
| 11. Round | 01/11/2008 | FC Pirin | - | Lokomotiv Plovdiv | 1:0 | ||||
| 13. Round | 15/11/2008 | Vihren Sandanski | - | Lokomotiv Plovdiv | 1:2 | ||||
| 16. Round | 06/03/2009 | Lokomotiv Plovdiv | - | OFC Sliven | 2:1 | ||||
| 18. Round | 18/03/2009 | Lokomotiv Plovdiv | - | CSKA Sofia | 1:3 | ||||
| 19. Round | 22/03/2009 | Levski Sofia | - | Lokomotiv Plovdiv | 1:0 | ||||
| 20. Round | 03/04/2009 | Lokomotiv Plovdiv | - | Spartak Varna | 2:1 | ||||
| 21. Round | 13/04/2009 | Cherno More Varna | - | Lokomotiv Plovdiv | 2:1 | ||||
| 23. Round | 22/04/2009 | Lokomotiv Sofia | - | Lokomotiv Plovdiv | 1:2 | ||||
| 28. Round | 23/05/2009 | Lokomotiv Plovdiv | - | Vihren Sandanski | 0:1 |  |
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| 29. Round | 31/05/2009 | Belasitsa Petrich | - | Lokomotiv Plovdiv | 1:2 |
Bulgaria