6. Round | 20/09/2008 | OFC Sliven | - | FC Pirin | 2:1 | ||||
7. Round | 27/09/2008 | FC Pirin | - | CSKA Sofia | 2:2 | ![]() |
|||
8. Round | 04/10/2008 | Spartak Varna | - | FC Pirin | 2:0 | ||||
9. Round | 21/10/2008 | FC Pirin | - | Slavia Sofia | 3:2 | ||||
10. Round | 25/10/2008 | Minyor Pernik | - | FC Pirin | 0:0 | ||||
11. Round | 01/11/2008 | FC Pirin | - | Lokomotiv Plovdiv | 1:0 | ![]() |
|||
12. Round | 07/11/2008 | FC Pirin | - | Vihren Sandanski | 2:1 | ||||
16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
17. Round | 13/03/2009 | Pirin Blagoevgrad | - | Lokomotiv Sofia | 0:4 |