1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
1. Round | 18/08/2018 | Chippa United | - | Black Leopards | 2:2 | ||||
3. Round | 03/10/2018 | Chippa United | - | Free State Stars | 1:0 | ||||
6. Round | 04/01/2019 | Chippa United | - | Bloemfontein Celtic | 0:1 | ||||
6. Round | 08/01/2019 | Orlando Pirates | - | Chippa United | 4:2 | ||||
9. Round | 23/04/2019 | Mamelodi Sundowns | - | Chippa United | 3:2 |