2. Round | 17/08/2008 | Lokomotiv Sofia | - | FC Pirin | 1:0 | ||||
3. Round | 23/08/2008 | FC Pirin | - | PFC Litex Lovech | 1:1 | ||||
5. Round | 15/09/2008 | FC Pirin | - | Belasitsa Petrich | 2:0 | ||||
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 | ||||
11. Round | 01/11/2008 | FC Pirin | - | Lokomotiv Plovdiv | 1:0 | ||||
12. Round | 07/11/2008 | FC Pirin | - | Vihren Sandanski | 2:1 | ||||
13. Round | 15/11/2008 | Botev Plovdiv | - | FC Pirin | 1:0 | ||||
14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
26. Round | 11/05/2009 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:2 | ||||
27. Round | 18/05/2009 | Vihren Sandanski | - | Pirin Blagoevgrad | 1:3 | ||||
28. Round | 23/05/2009 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:3 | ||||
30. Round | 13/06/2009 | Pirin Blagoevgrad | - | Levski Sofia | 1:1 |