| 1. Round | 04/08/2018 | Mamelodi Sundowns | - | Kaizer Chiefs | 1:1 | ||||
| 1. Round | 07/08/2018 | Kaizer Chiefs | - | BidVest Wits | 1:3 | ||||
| 1. Round | 14/08/2018 | Baroka FC | - | Kaizer Chiefs | 1:1 | ||||
| 1. Round | 17/08/2018 | Maritzburg United | - | Kaizer Chiefs | 0:0 | ||||
| 1. Round | 29/08/2018 | Kaizer Chiefs | - | Bloemfontein Celtic | 2:2 | ||||
| 2. Round | 15/09/2018 | Cape Town City FC | - | Kaizer Chiefs | 1:4 | ||||
| 2. Round | 22/09/2018 | Kaizer Chiefs | - | AmaZulu FC | 2:0 | ||||
| 3. Round | 02/10/2018 | Highlands Park | - | Kaizer Chiefs | 0:0 | ||||
| 3. Round | 06/10/2018 | Kaizer Chiefs | - | Polokwane City FC | 0:1 | ||||
| 3. Round | 27/10/2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
| 5. Round | 12/12/2018 | Kaizer Chiefs | - | SuperSport United | 1:0 | ||||
| 6. Round | 30/01/2019 | Kaizer Chiefs | - | Cape Town City FC | 0:1 | ||||
| 7. Round | 23/02/2019 | Polokwane City FC | - | Kaizer Chiefs | 1:1 | ||||
| 9. Round | 27/04/2019 | Bloemfontein Celtic | - | Kaizer Chiefs | 1:0 |
South Africa