| 3. Round | 29/07/2023 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:0 |  |
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| 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 | ||||
| 16. Round | 03/11/2023 | PFC Beroe | - | Pirin Blagoevgrad | 0:0 | ||||
| 17. Round | 11/11/2023 | Pirin Blagoevgrad | - | CSKA 1948 Sofia | 2:1 | |
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| 19. Round | 03/12/2023 | Pirin Blagoevgrad | - | Lokomotiv Sofia | 1:1 | ||||
| 20. Round | 11/12/2023 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:0 | ||||
| 21. Round | 17/02/2024 | Pirin Blagoevgrad | - | Levski Sofia | 1:2 | |
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| 22. Round | 23/02/2024 | Botev Vratsa | - | Pirin Blagoevgrad | 1:2 | ||||
| 23. Round | 04/03/2024 | Arda Kardzhali | - | Pirin Blagoevgrad | 0:0 | |
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| 24. Round | 11/03/2024 | Pirin Blagoevgrad | - | Hebar Pazardzhik | 1:1 | ||||
| 27. Round | 02/04/2024 | Slavia Sofia | - | Pirin Blagoevgrad | 0:0 | ||||
| 28. Round | 07/04/2024 | Pirin Blagoevgrad | - | PFC Ludogorets Razgrad | 0:2 | ||||
| 29. Round | 12/04/2024 | CSKA Sofia | - | Pirin Blagoevgrad | 1:2 |
Bulgaria