| 1. Round | 14/07/2023 | FK Krumovgrad | - | PFC Ludogorets Razgrad | 3:1 | ||||
| 5. Round | 14/08/2023 | FK Krumovgrad | - | CSKA 1948 Sofia | 1:0 |  |
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| 6. Round | 20/08/2023 | Botev Plovdiv | - | FK Krumovgrad | 1:2 | ||||
| 7. Round | 26/08/2023 | FK Krumovgrad | - | Lokomotiv Sofia | 2:0 | ||||
| 8. Round | 03/09/2023 | Lokomotiv Plovdiv | - | FK Krumovgrad | 4:0 | ||||
| 9. Round | 18/09/2023 | FK Krumovgrad | - | Levski Sofia | 2:2 | |
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| 10. Round | 24/09/2023 | Pirin Blagoevgrad | - | FK Krumovgrad | 1:0 | ||||
| 11. Round | 28/09/2023 | FK Krumovgrad | - | Arda Kardzhali | 1:3 | ||||
| 12. Round | 02/10/2023 | Hebar Pazardzhik | - | FK Krumovgrad | 0:0 | |
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| 13. Round | 06/10/2023 | FK Krumovgrad | - | Botev Vratsa | 1:0 | ||||
| 14. Round | 20/10/2023 | FK Krumovgrad | - | Etar Veliko Tarnovo | 0:0 | ||||
| 15. Round | 27/10/2023 | Slavia Sofia | - | FK Krumovgrad | 2:0 | |
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| 16. Round | 05/11/2023 | PFC Ludogorets Razgrad | - | FK Krumovgrad | 1:0 | |
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| 21. Round | 17/02/2024 | FK Krumovgrad | - | Botev Plovdiv | 2:1 | ||||
| 22. Round | 25/02/2024 | Lokomotiv Sofia | - | FK Krumovgrad | 0:2 | ||||
| 25. Round | 17/03/2024 | FK Krumovgrad | - | Pirin Blagoevgrad | 2:2 | |
Bulgaria