| 6. Round | 16/08/2019 | Etar Veliko Tarnovo | - | Tsarsko Selo Sofia | 1:1 | ||||
| 7. Round | 23/08/2019 | Tsarsko Selo Sofia | - | PFC Beroe | 2:1 |  |
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| 8. Round | 01/09/2019 | Vitosha Bistritsa | - | Tsarsko Selo Sofia | 3:2 | ||||
| 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 |  |
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| 12. Round | 04/10/2019 | Slavia Sofia | - | Tsarsko Selo Sofia | 1:0 | ||||
| 13. Round | 21/10/2019 | Tsarsko Selo Sofia | - | Botev Vratsa | 3:0 | |
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| 14. Round | 29/10/2019 | Tsarsko Selo Sofia | - | PFC Ludogorets Razgrad | 0:2 | ||||
| 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 | ||||
| 18. Round | 30/11/2019 | Tsarsko Selo Sofia | - | Botev Plovdiv | 0:3 | ||||
| 20. Round | 14/12/2019 | PFC Beroe | - | Tsarsko Selo Sofia | 2:0 |
Bulgaria