| 2. Round | 21/07/2019 | Olimpija Ljubljana | - | NK Domžale | 4:2 | ||||
| 4. Round | 04/08/2019 | Olimpija Ljubljana | - | NK Triglav | 4:2 | ||||
| 8. Round | 31/08/2019 | NK Tabor Sežana | - | Olimpija Ljubljana | 1:2 | ||||
| 10. Round | 22/09/2019 | Olimpija Ljubljana | - | NK Bravo | 3:1 | ||||
| 19. Round | 01/12/2019 | NK Bravo | - | Olimpija Ljubljana | 1:2 | ||||
| 20. Round | 04/12/2019 | Olimpija Ljubljana | - | NK Domžale | 0:1 |  |
Slovenia