| 1. Round | 14/07/2019 | Cherno More Varna | - | Lokomotiv Plovdiv | 3:1 | ||||
| 2. Round | 20/07/2019 | CSKA Sofia | - | Cherno More Varna | 1:3 | ||||
| 3. Round | 27/07/2019 | Cherno More Varna | - | Etar Veliko Tarnovo | 1:1 | ||||
| 10. Round | 20/09/2019 | Cherno More Varna | - | Botev Plovdiv | 2:0 | ||||
| 11. Round | 27/09/2019 | Tsarsko Selo Sofia | - | Cherno More Varna | 1:1 |  |
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| 12. Round | 04/10/2019 | Cherno More Varna | - | PFC Beroe | 2:0 | ||||
| 13. Round | 18/10/2019 | Vitosha Bistritsa | - | Cherno More Varna | 0:2 | ||||
| 17. Round | 23/11/2019 | Slavia Sofia | - | Cherno More Varna | 0:1 | ||||
| 18. Round | 30/11/2019 | Cherno More Varna | - | Botev Vratsa | 4:1 | ||||
| 19. Round | 07/12/2019 | PFC Ludogorets Razgrad | - | Cherno More Varna | 1:1 | ||||
| 20. Round | 14/12/2019 | Cherno More Varna | - | Arda Kardzhali | 1:1 | ||||
| 21. Round | 16/02/2020 | FC Dunav Ruse | - | Cherno More Varna | 0:2 | |
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| 22. Round | 22/02/2020 | Cherno More Varna | - | Levski Sofia | 2:2 | ||||
| 23. Round | 29/02/2020 | Botev Plovdiv | - | Cherno More Varna | 1:1 | ||||
| 24. Round | 06/03/2020 | Cherno More Varna | - | Tsarsko Selo Sofia | 1:0 | |
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| 25. Round | 07/06/2020 | PFC Beroe | - | Cherno More Varna | 3:0 |  |
Bulgaria