| 6. Round | 09/01/2019 | Maritzburg United | - | Free State Stars | 1:2 | ||||
| 7. Round | 24/02/2019 | Bloemfontein Celtic | - | Free State Stars | 2:3 | ||||
| 8. Round | 16/03/2019 | Free State Stars | - | AmaZulu FC | 4:1 | ||||
| 9. Round | 13/04/2019 | Orlando Pirates | - | Free State Stars | 2:1 |  |
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| 9. Round | 24/04/2019 | Free State Stars | - | Baroka FC | 2:2 |  |
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| 9. Round | 28/04/2019 | Golden Arrows | - | Free State Stars | 2:1 | ||||
| 10. Round | 11/05/2019 | Free State Stars | - | Mamelodi Sundowns | 0:1 |
South Africa