| 4. Round | 05/08/2023 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 8. Round | 01/09/2023 | Pirin Blagoevgrad | - | Arda Kardzhali | 0:2 | ||||
| 11. Round | 28/09/2023 | Etar Veliko Tarnovo | - | Pirin Blagoevgrad | 0:2 | ||||
| 12. Round | 02/10/2023 | Pirin Blagoevgrad | - | Slavia Sofia | 1:1 | ||||
| 13. Round | 08/10/2023 | PFC Ludogorets Razgrad | - | Pirin Blagoevgrad | 4:0 | ||||
| 14. Round | 21/10/2023 | Pirin Blagoevgrad | - | CSKA Sofia | 1:2 | ||||
| 15. Round | 26/10/2023 | Cherno More Varna | - | Pirin Blagoevgrad | 2:1 | ||||
| 18. Round | 25/11/2023 | Botev Plovdiv | - | Pirin Blagoevgrad | 3:1 | ||||
| 20. Round | 11/12/2023 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:0 |
Bulgaria