| 10. Round | 28/09/2018 | Vitosha Bistritsa | - | Septemvri Sofia | 2:1 | ||||
| 11. Round | 06/10/2018 | Septemvri Sofia | - | CSKA Sofia | 0:3 | ||||
| 12. Round | 20/10/2018 | Slavia Sofia | - | Septemvri Sofia | 3:1 | ||||
| 13. Round | 28/10/2018 | Septemvri Sofia | - | PFC Ludogorets Razgrad | 1:4 | ||||
| 14. Round | 03/11/2018 | Septemvri Sofia | - | FK Vereya | 1:0 | ||||
| 15. Round | 10/11/2018 | Botev Plovdiv | - | Septemvri Sofia | 2:0 | ||||
| 16. Round | 24/11/2018 | Septemvri Sofia | - | Cherno More Varna | 2:1 | ||||
| 17. Round | 02/12/2018 | Botev Vratsa | - | Septemvri Sofia | 4:1 | ||||
| 18. Round | 05/12/2018 | Septemvri Sofia | - | Levski Sofia | 2:2 |  |
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| 19. Round | 09/12/2018 | Septemvri Sofia | - | FC Dunav Ruse | 2:1 | |
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| 20. Round | 16/12/2018 | Etar Veliko Tarnovo | - | Septemvri Sofia | 2:0 | ||||
| 21. Round | 17/02/2019 | Septemvri Sofia | - | PFC Beroe | 1:0 | ||||
| 22. Round | 20/02/2019 | Lokomotiv Plovdiv | - | Septemvri Sofia | 0:2 | ||||
| 23. Round | 25/02/2019 | Septemvri Sofia | - | Vitosha Bistritsa | 0:0 | ||||
| 24. Round | 02/03/2019 | CSKA Sofia | - | Septemvri Sofia | 5:1 | ||||
| 25. Round | 10/03/2019 | Septemvri Sofia | - | Slavia Sofia | 1:2 | ||||
| 26. Round | 16/03/2019 | PFC Ludogorets Razgrad | - | Septemvri Sofia | 6:0 |
Bulgaria