| 1. Round | 10/08/2019 | Kaizer Chiefs | - | Black Leopards | 1:0 | ||||
| 1. Round | 24/08/2019 | Kaizer Chiefs | - | SuperSport United | 1:1 | ||||
| 1. Round | 27/08/2019 | Cape Town City FC | - | Kaizer Chiefs | 1:2 |  |
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| 2. Round | 14/09/2019 | Kaizer Chiefs | - | Polokwane City FC | 0:1 | ||||
| 2. Round | 24/09/2019 | AmaZulu FC | - | Kaizer Chiefs | 0:2 | ||||
| 4. Round | 06/11/2019 | Chippa United | - | Kaizer Chiefs | 0:2 | ||||
| 4. Round | 09/11/2019 | Kaizer Chiefs | - | Orlando Pirates | 3:2 | ||||
| 4. Round | 27/11/2019 | Stellenbosch FC | - | Kaizer Chiefs | 0:4 | ||||
| 6. Round | 08/01/2020 | Kaizer Chiefs | - | Highlands Park | 3:0 | ||||
| 6. Round | 12/01/2020 | Kaizer Chiefs | - | Cape Town City FC | 3:0 | ||||
| 6. Round | 18/01/2020 | Black Leopards | - | Kaizer Chiefs | 1:1 | ||||
| 6. Round | 25/01/2020 | Golden Arrows | - | Kaizer Chiefs | 0:1 | |
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| 7. Round | 15/02/2020 | Kaizer Chiefs | - | Maritzburg United | 1:2 | ||||
| 8. Round | 07/03/2020 | Kaizer Chiefs | - | AmaZulu FC | 0:1 | ||||
| 9. Round | 12/08/2020 | Kaizer Chiefs | - | BidVest Wits | 1:1 | ||||
| 9. Round | 23/08/2020 | Kaizer Chiefs | - | Stellenbosch FC | 1:1 |
South Africa