| 1. Round | 23/07/2018 | FK Vereya | - | Septemvri Sofia | 0:0 | ||||
| 2. Round | 28/07/2018 | Septemvri Sofia | - | Botev Plovdiv | 0:2 | ||||
| 4. Round | 13/08/2018 | Septemvri Sofia | - | Botev Vratsa | 1:2 | ||||
| 7. Round | 01/09/2018 | Septemvri Sofia | - | Etar Veliko Tarnovo | 0:2 | ||||
| 18. Round | 05/12/2018 | Septemvri Sofia | - | Levski Sofia | 2:2 | ||||
| 20. Round | 16/12/2018 | Etar Veliko Tarnovo | - | Septemvri Sofia | 2:0 | ||||
| 21. Round | 17/02/2019 | Septemvri Sofia | - | PFC Beroe | 1:0 | ||||
| 24. Round | 02/03/2019 | CSKA Sofia | - | Septemvri Sofia | 5:1 |
Bulgaria