| 2. Round | 20/07/2019 | CSKA Sofia | - | Cherno More Varna | 1:3 |  |
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| 3. Round | 28/07/2019 | Slavia Sofia | - | CSKA Sofia | 1:2 | ||||
| 4. Round | 04/08/2019 | CSKA Sofia | - | Botev Vratsa | 1:0 | ||||
| 5. Round | 11/08/2019 | PFC Ludogorets Razgrad | - | CSKA Sofia | 0:0 | ||||
| 6. Round | 18/08/2019 | CSKA Sofia | - | Arda Kardzhali | 3:2 | |
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| 7. Round | 25/08/2019 | FC Dunav Ruse | - | CSKA Sofia | 1:1 | ||||
| 8. Round | 01/09/2019 | CSKA Sofia | - | Levski Sofia | 2:2 | ||||
| 9. Round | 14/09/2019 | Botev Plovdiv | - | CSKA Sofia | 0:1 | ||||
| 11. Round | 29/09/2019 | PFC Beroe | - | CSKA Sofia | 2:1 | ||||
| 12. Round | 05/10/2019 | CSKA Sofia | - | Vitosha Bistritsa | 4:0 | |
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| 13. Round | 20/10/2019 | Lokomotiv Plovdiv | - | CSKA Sofia | 1:0 | ||||
| 14. Round | 30/10/2019 | Etar Veliko Tarnovo | - | CSKA Sofia | 0:4 | ||||
| 15. Round | 05/11/2019 | Cherno More Varna | - | CSKA Sofia | 0:2 | ||||
| 19. Round | 08/12/2019 | Arda Kardzhali | - | CSKA Sofia | 0:0 | ||||
| 20. Round | 14/12/2019 | CSKA Sofia | - | FC Dunav Ruse | 4:0 |
Scotland
