| 3. Round | 06/10/2018 | Free State Stars | - | Bloemfontein Celtic | 2:0 | ||||
| 3. Round | 24/10/2018 | Free State Stars | - | Golden Arrows | 1:1 | ||||
| 3. Round | 28/10/2018 | Black Leopards | - | Free State Stars | 1:1 | ||||
| 4. Round | 07/11/2018 | Mamelodi Sundowns | - | Free State Stars | 3:1 | ||||
| 4. Round | 10/11/2018 | Free State Stars | - | SuperSport United | 0:1 | ||||
| 5. Round | 11/12/2018 | Free State Stars | - | Orlando Pirates | 1:3 |  |
|||
| 7. Round | 09/02/2019 | Free State Stars | - | Chippa United | 0:2 | ||||
| 7. Round | 24/02/2019 | Bloemfontein Celtic | - | Free State Stars | 2:3 | ||||
| 8. Round | 06/03/2019 | Free State Stars | - | Polokwane City FC | 1:1 | ||||
| 9. Round | 28/04/2019 | Golden Arrows | - | Free State Stars | 2:1 |
South Africa