| 1. Round | 08/08/2018 | Free State Stars | - | Maritzburg United | 2:1 | ||||
| 1. Round | 19/08/2018 | AmaZulu FC | - | Free State Stars | 2:1 | ||||
| 1. Round | 29/08/2018 | Free State Stars | - | Cape Town City FC | 2:2 | ||||
| 2. Round | 15/09/2018 | Polokwane City FC | - | Free State Stars | 1:0 |  |
|||
| 2. Round | 18/09/2018 | Free State Stars | - | Kaizer Chiefs | 0:2 | ||||
| 2. Round | 22/09/2018 | Free State Stars | - | Highlands Park | 1:0 |  |
|||
| 2. Round | 26/09/2018 | Baroka FC | - | Free State Stars | 0:0 | ||||
| 3. Round | 03/10/2018 | Chippa United | - | Free State Stars | 1:0 | ||||
| 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 | 10/11/2018 | Free State Stars | - | SuperSport United | 0:1 | ||||
| 5. Round | 11/12/2018 | Free State Stars | - | Orlando Pirates | 1:3 | ||||
| 6. Round | 05/01/2019 | Free State Stars | - | BidVest Wits | 1:2 | |
South Africa