1. Round | 05/08/2018 | Bloemfontein Celtic | - | Chippa United | 2:0 | ||||
1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
1. Round | 18/08/2018 | Chippa United | - | Black Leopards | 2:2 | ||||
1. Round | 29/08/2018 | SuperSport United | - | Chippa United | 2:1 | ||||
2. Round | 15/09/2018 | Chippa United | - | Baroka FC | 1:0 | ||||
3. Round | 06/10/2018 | Highlands Park | - | Chippa United | 2:1 | ||||
3. Round | 27/10/2018 | Chippa United | - | Mamelodi Sundowns | 0:1 | ||||
4. Round | 27/11/2018 | Maritzburg United | - | Chippa United | 0:0 | ||||
5. Round | 21/12/2018 | BidVest Wits | - | Chippa United | 2:0 | ||||
6. Round | 19/01/2019 | Chippa United | - | Maritzburg United | 2:0 | ||||
7. Round | 22/02/2019 | Chippa United | - | Golden Arrows | 1:1 | ||||
9. Round | 06/04/2019 | AmaZulu FC | - | Chippa United | 0:1 | ||||
9. Round | 23/04/2019 | Mamelodi Sundowns | - | Chippa United | 3:2 | ||||
10. Round | 04/05/2019 | Polokwane City FC | - | Chippa United | 1:3 |