| 1. Round | 09/08/2008 | OFC Sliven | - | Lokomotiv Plovdiv | 1:1 | ||||
| 2. Round | 16/08/2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 | ||||
| 3. Round | 24/08/2008 | CSKA Sofia | - | Lokomotiv Plovdiv | 2:0 | ||||
| 4. Round | 31/08/2008 | Lokomotiv Plovdiv | - | Levski Sofia | 2:3 | ||||
| 5. Round | 13/09/2008 | Spartak Varna | - | Lokomotiv Plovdiv | 1:1 | ||||
| 6. Round | 21/09/2008 | Lokomotiv Plovdiv | - | Cherno More Varna | 1:0 | ||||
| 7. Round | 28/09/2008 | Slavia Sofia | - | Lokomotiv Plovdiv | 2:0 | ||||
| 8. Round | 03/10/2008 | Lokomotiv Plovdiv | - | Lokomotiv Sofia | 3:2 | ||||
| 9. Round | 19/10/2008 | Minyor Pernik | - | Lokomotiv Plovdiv | 2:2 | ||||
| 11. Round | 01/11/2008 | FC Pirin | - | Lokomotiv Plovdiv | 1:0 | ||||
| 12. Round | 08/11/2008 | Lokomotiv Plovdiv | - | Lokomotiv 2012 Mezdra | 0:2 | ||||
| 15. Round | 29/11/2008 | Botev Plovdiv | - | Lokomotiv Plovdiv | 2:2 |
Bulgaria