| 6. Round | 18/08/2019 | NK Aluminij | - | Olimpija Ljubljana | 1:0 | ||||
| 7. Round | 24/08/2019 | Olimpija Ljubljana | - | NŠ Mura | 1:1 | ||||
| 9. Round | 15/09/2019 | Olimpija Ljubljana | - | NK Celje | 2:2 | ||||
| 10. Round | 22/09/2019 | Olimpija Ljubljana | - | NK Bravo | 3:1 | ||||
| 13. Round | 06/10/2019 | NK Triglav | - | Olimpija Ljubljana | 2:3 |  |
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| 14. Round | 19/10/2019 | Olimpija Ljubljana | - | Rudar Velenje | 6:0 | ||||
| 16. Round | 03/11/2019 | NŠ Mura | - | Olimpija Ljubljana | 3:1 |
Slovenia