| 1. Round | 14/07/2023 | Pirin Blagoevgrad | - | PFC Beroe | 1:2 |  |
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| 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 | ||||
| 6. Round | 14/09/2023 | Levski Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 9. Round | 18/09/2023 | Hebar Pazardzhik | - | Pirin Blagoevgrad | 1:2 | ||||
| 10. Round | 24/09/2023 | Pirin Blagoevgrad | - | FK Krumovgrad | 1:0 | ||||
| 11. Round | 28/09/2023 | Etar Veliko Tarnovo | - | Pirin Blagoevgrad | 0:2 | ||||
| 12. Round | 02/10/2023 | Pirin Blagoevgrad | - | Slavia Sofia | 1:1 | ||||
| 14. Round | 21/10/2023 | Pirin Blagoevgrad | - | CSKA Sofia | 1:2 | ||||
| 20. Round | 11/12/2023 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:0 |
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