1. Round | 05/08/2018 | Bloemfontein Celtic | - | Chippa United | 2:0 | ||||
1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
2. Round | 22/09/2018 | Golden Arrows | - | Chippa United | 0:0 | ||||
6. Round | 04/01/2019 | Chippa United | - | Bloemfontein Celtic | 0:1 | ||||
6. Round | 08/01/2019 | Orlando Pirates | - | Chippa United | 4:2 | ||||
7. Round | 09/02/2019 | Free State Stars | - | Chippa United | 0:2 | ||||
7. Round | 22/02/2019 | Chippa United | - | Golden Arrows | 1:1 | ||||
8. Round | 03/03/2019 | Chippa United | - | SuperSport United | 0:1 | ||||
8. Round | 10/03/2019 | Black Leopards | - | Chippa United | 3:2 | ||||
9. Round | 23/04/2019 | Mamelodi Sundowns | - | Chippa United | 3:2 | ||||
9. Round | 26/04/2019 | Chippa United | - | Cape Town City FC | 0:2 | ||||
10. Round | 04/05/2019 | Polokwane City FC | - | Chippa United | 1:3 | ||||
10. Round | 11/05/2019 | Chippa United | - | Kaizer Chiefs | 1:0 |