| 1. Ronde | 14.07.2023 | FK Krumovgrad | - | PFC Ludogorets Razgrad | 3:1 | ||||
| 2. Ronde | 21.07.2023 | CSKA Sofia | - | FK Krumovgrad | 1:0 |  |
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| 5. Ronde | 14.08.2023 | FK Krumovgrad | - | CSKA 1948 Sofia | 1:0 | ||||
| 10. Ronde | 24.09.2023 | Pirin Blagoevgrad | - | FK Krumovgrad | 1:0 | ||||
| 11. Ronde | 28.09.2023 | FK Krumovgrad | - | Arda Kardzhali | 1:3 | |
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| 12. Ronde | 02.10.2023 | Hebar Pazardzhik | - | FK Krumovgrad | 0:0 | ||||
| 13. Ronde | 06.10.2023 | FK Krumovgrad | - | Botev Vratsa | 1:0 | ||||
| 14. Ronde | 20.10.2023 | FK Krumovgrad | - | Etar Veliko Tarnovo | 0:0 |
Bulgarije