| 4. Round | 05/08/2019 | Tsarsko Selo Sofia | - | Levski Sofia | 0:2 | ||||
| 5. Round | 10/08/2019 | Botev Plovdiv | - | Tsarsko Selo Sofia | 0:2 |  |
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| 6. Round | 16/08/2019 | Etar Veliko Tarnovo | - | Tsarsko Selo Sofia | 1:1 | |
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| 7. Round | 23/08/2019 | Tsarsko Selo Sofia | - | PFC Beroe | 2:1 | ||||
| 8. Round | 01/09/2019 | Vitosha Bistritsa | - | Tsarsko Selo Sofia | 3:2 | ||||
| 9. Round | 13/09/2019 | Tsarsko Selo Sofia | - | Lokomotiv Plovdiv | 2:3 | ||||
| 10. Round | 20/09/2019 | CSKA Sofia | - | Tsarsko Selo Sofia | 3:0 | ||||
| 11. Round | 27/09/2019 | Tsarsko Selo Sofia | - | Cherno More Varna | 1:1 | ||||
| 12. Round | 04/10/2019 | Slavia Sofia | - | Tsarsko Selo Sofia | 1:0 | |
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| 13. Round | 21/10/2019 | Tsarsko Selo Sofia | - | Botev Vratsa | 3:0 | ||||
| 15. Round | 07/11/2019 | Arda Kardzhali | - | Tsarsko Selo Sofia | 0:2 | ||||
| 16. Round | 11/11/2019 | Tsarsko Selo Sofia | - | FC Dunav Ruse | 1:2 | ||||
| 17. Round | 24/11/2019 | Levski Sofia | - | Tsarsko Selo Sofia | 2:0 | |
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| 19. Round | 06/12/2019 | Tsarsko Selo Sofia | - | Etar Veliko Tarnovo | 2:2 |  |
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| 20. Round | 14/12/2019 | PFC Beroe | - | Tsarsko Selo Sofia | 2:0 | |
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