| 3. Round | 26/07/2019 | FC Dunav Ruse | - | Tsarsko Selo Sofia | 3:1 | ||||
| 4. Round | 05/08/2019 | Tsarsko Selo Sofia | - | Levski Sofia | 0:2 |  |
|||
| 5. Round | 10/08/2019 | Botev Plovdiv | - | Tsarsko Selo Sofia | 0:2 | ||||
| 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 | ||||
| 9. Round | 13/09/2019 | Tsarsko Selo Sofia | - | Lokomotiv Plovdiv | 2:3 | ||||
| 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 | ||||
| 15. Round | 07/11/2019 | Arda Kardzhali | - | Tsarsko Selo Sofia | 0:2 | ||||
| 19. Round | 06/12/2019 | Tsarsko Selo Sofia | - | Etar Veliko Tarnovo | 2:2 | ||||
| 20. Round | 14/12/2019 | PFC Beroe | - | Tsarsko Selo Sofia | 2:0 | |
|||
| 21. Round | 14/02/2020 | Tsarsko Selo Sofia | - | Vitosha Bistritsa | 1:0 | |
|||
| 22. Round | 23/02/2020 | Lokomotiv Plovdiv | - | Tsarsko Selo Sofia | 4:0 | |
|||
| 24. Round | 06/03/2020 | Cherno More Varna | - | Tsarsko Selo Sofia | 1:0 | ||||
| 25. Round | 08/06/2020 | Tsarsko Selo Sofia | - | Slavia Sofia | 1:3 | ||||
| 26. Round | 12/06/2020 | Botev Vratsa | - | Tsarsko Selo Sofia | 0:1 |
Bulgaria