| 1. Round | 14/07/2023 | Pirin Blagoevgrad | - | PFC Beroe | 1:2 | ||||
| 2. Round | 21/07/2023 | CSKA 1948 Sofia | - | Pirin Blagoevgrad | 3:0 | ||||
| 3. Round | 29/07/2023 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:0 | ||||
| 4. Round | 05/08/2023 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 5. Round | 11/08/2023 | Pirin Blagoevgrad | - | Lokomotiv Plovdiv | 0:1 | ||||
| 7. Round | 25/08/2023 | Pirin Blagoevgrad | - | Botev Vratsa | 0:1 | ||||
| 8. Round | 01/09/2023 | Pirin Blagoevgrad | - | Arda Kardzhali | 0:2 | ||||
| 9. Round | 18/09/2023 | Hebar Pazardzhik | - | Pirin Blagoevgrad | 1:2 | ||||
| 15. Round | 26/10/2023 | Cherno More Varna | - | Pirin Blagoevgrad | 2:1 | ||||
| 16. Round | 03/11/2023 | PFC Beroe | - | Pirin Blagoevgrad | 0:0 | ||||
| 17. Round | 11/11/2023 | Pirin Blagoevgrad | - | CSKA 1948 Sofia | 2:1 | ||||
| 18. Round | 25/11/2023 | Botev Plovdiv | - | Pirin Blagoevgrad | 3:1 |
Bulgaria