2. Round | 18/09/2018 | Free State Stars | - | Kaizer Chiefs | 0:2 | ||||
3. Round | 06/10/2018 | Kaizer Chiefs | - | Polokwane City FC | 0:1 | ||||
3. Round | 27/10/2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
4. Round | 07/11/2018 | Kaizer Chiefs | - | Black Leopards | 1:0 | ||||
4. Round | 10/11/2018 | Kaizer Chiefs | - | Chippa United | 0:0 | ||||
5. Round | 12/12/2018 | Kaizer Chiefs | - | SuperSport United | 1:0 | ||||
6. Round | 05/01/2019 | Kaizer Chiefs | - | Mamelodi Sundowns | 1:2 | ||||
6. Round | 09/01/2019 | BidVest Wits | - | Kaizer Chiefs | 0:2 | ||||
6. Round | 16/01/2019 | AmaZulu FC | - | Kaizer Chiefs | 2:3 | ||||
8. Round | 02/03/2019 | Kaizer Chiefs | - | Highlands Park | 3:2 | ||||
9. Round | 13/04/2019 | Black Leopards | - | Kaizer Chiefs | 1:1 |