| 3. Round | 04/08/2018 | Cherno More Varna | - | Septemvri Sofia | 1:5 |  |
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| 4. Round | 13/08/2018 | Septemvri Sofia | - | Botev Vratsa | 1:2 | ||||
| 5. Round | 19/08/2018 | Levski Sofia | - | Septemvri Sofia | 2:0 | ||||
| 6. Round | 24/08/2018 | FC Dunav Ruse | - | Septemvri Sofia | 2:0 | ||||
| 7. Round | 01/09/2018 | Septemvri Sofia | - | Etar Veliko Tarnovo | 0:2 | ||||
| 8. Round | 15/09/2018 | PFC Beroe | - | Septemvri Sofia | 1:0 | ||||
| 9. Round | 22/09/2018 | Septemvri Sofia | - | Lokomotiv Plovdiv | 1:3 | ||||
| 10. Round | 28/09/2018 | Vitosha Bistritsa | - | Septemvri Sofia | 2:1 | ||||
| 12. Round | 20/10/2018 | Slavia Sofia | - | Septemvri Sofia | 3:1 |
Bulgaria