| 4. Round | 04/08/2019 | Olimpija Ljubljana | - | NK Triglav | 4:2 | ||||
| 5. Round | 11/08/2019 | Rudar Velenje | - | Olimpija Ljubljana | 0:3 | ||||
| 7. Round | 24/08/2019 | Olimpija Ljubljana | - | NŠ Mura | 1:1 |  |
|||
| 8. Round | 31/08/2019 | NK Tabor Sežana | - | Olimpija Ljubljana | 1:2 | ||||
| 9. Round | 15/09/2019 | Olimpija Ljubljana | - | NK Celje | 2:2 | |
|||
| 26. Round | 06/06/2020 | NK Tabor Sežana | - | Olimpija Ljubljana | 0:3 | ||||
| 27. Round | 13/06/2020 | Olimpija Ljubljana | - | NK Celje | 0:1 | ||||
| 28. Round | 17/06/2020 | Olimpija Ljubljana | - | NK Bravo | 0:5 | ||||
| 29. Round | 21/06/2020 | NK Domžale | - | Olimpija Ljubljana | 0:1 | ||||
| 30. Round | 28/06/2020 | Olimpija Ljubljana | - | NK Maribor | 1:0 | ||||
| 31. Round | 05/07/2020 | NK Triglav | - | Olimpija Ljubljana | 3:7 | ||||
| 32. Round | 09/07/2020 | Olimpija Ljubljana | - | Rudar Velenje | 5:0 | ||||
| 33. Round | 12/07/2020 | Olimpija Ljubljana | - | NK Aluminij | 0:1 | ||||
| 34. Round | 16/07/2020 | NŠ Mura | - | Olimpija Ljubljana | 1:1 | |
|||
| 35. Round | 19/07/2020 | Olimpija Ljubljana | - | NK Tabor Sežana | 1:2 | ||||
| 36. Round | 22/07/2020 | NK Celje | - | Olimpija Ljubljana | 2:2 | |
Slovenia