| 1. Round | 13/07/2019 | PFC Ludogorets Razgrad | - | Tsarsko Selo Sofia | 2:0 |  |
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| 2. Round | 19/07/2019 | Tsarsko Selo Sofia | - | Arda Kardzhali | 0:0 | ||||
| 3. Round | 26/07/2019 | FC Dunav Ruse | - | Tsarsko Selo Sofia | 3:1 | |
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| 4. Round | 05/08/2019 | Tsarsko Selo Sofia | - | Levski Sofia | 0:2 | |
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| 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 | ||||
| 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 | ||||
| 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 | |
Bulgaria