| 1. Jornada | 14.07.2023 | Pirin Blagoevgrad | - | PFC Beroe | 1:2 |  |
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| 2. Jornada | 21.07.2023 | CSKA 1948 Sofia | - | Pirin Blagoevgrad | 3:0 | ||||
| 3. Jornada | 29.07.2023 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:0 | ||||
| 4. Jornada | 05.08.2023 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 5. Jornada | 11.08.2023 | Pirin Blagoevgrad | - | Lokomotiv Plovdiv | 0:1 | ||||
| 7. Jornada | 25.08.2023 | Pirin Blagoevgrad | - | Botev Vratsa | 0:1 | ||||
| 8. Jornada | 01.09.2023 | Pirin Blagoevgrad | - | Arda Kardzhali | 0:2 | ||||
| 6. Jornada | 14.09.2023 | Levski Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 9. Jornada | 18.09.2023 | Hebar Pazardzhik | - | Pirin Blagoevgrad | 1:2 | ||||
| 10. Jornada | 24.09.2023 | Pirin Blagoevgrad | - | FK Krumovgrad | 1:0 | ||||
| 11. Jornada | 28.09.2023 | Etar Veliko Tarnovo | - | Pirin Blagoevgrad | 0:2 | ||||
| 12. Jornada | 02.10.2023 | Pirin Blagoevgrad | - | Slavia Sofia | 1:1 | ||||
| 14. Jornada | 21.10.2023 | Pirin Blagoevgrad | - | CSKA Sofia | 1:2 | ||||
| 20. Jornada | 11.12.2023 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:0 |
Ucrania