| 22. Round | 23/02/2024 | Botev Vratsa | - | Pirin Blagoevgrad | 1:2 | ||||
| 23. Round | 04/03/2024 | Arda Kardzhali | - | Pirin Blagoevgrad | 0:0 | ||||
| 25. Round | 17/03/2024 | FK Krumovgrad | - | Pirin Blagoevgrad | 2:2 | ||||
| 28. Round | 07/04/2024 | Pirin Blagoevgrad | - | PFC Ludogorets Razgrad | 0:2 | ||||
| 29. Round | 12/04/2024 | CSKA Sofia | - | Pirin Blagoevgrad | 1:2 | ||||
| 30. Round | 20/04/2024 | Pirin Blagoevgrad | - | Cherno More Varna | 0:0 |
Portugal