| 1. Round | 03/08/2019 | Chippa United | - | Stellenbosch FC | 0:0 | ||||
| 1. Round | 14/08/2019 | Chippa United | - | Mamelodi Sundowns | 1:1 | ||||
| 1. Round | 24/08/2019 | Golden Arrows | - | Chippa United | 2:1 | ||||
| 2. Round | 14/09/2019 | Orlando Pirates | - | Chippa United | 2:1 | ||||
| 2. Round | 21/09/2019 | Chippa United | - | Bloemfontein Celtic | 0:0 | ||||
| 2. Round | 27/09/2019 | Maritzburg United | - | Chippa United | 1:0 | ||||
| 3. Round | 01/10/2019 | Chippa United | - | BidVest Wits | 0:1 | ||||
| 4. Round | 27/11/2019 | Chippa United | - | Black Leopards | 3:0 |
South Africa