| 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 | ||||
| 3. Round | 01/10/2019 | Chippa United | - | BidVest Wits | 0:1 |  |
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| 3. Round | 26/10/2019 | Highlands Park | - | Chippa United | 2:0 | ||||
| 4. Round | 06/11/2019 | Chippa United | - | Kaizer Chiefs | 0:2 | ||||
| 7. Round | 01/02/2020 | Chippa United | - | Orlando Pirates | 1:2 | ||||
| 9. Round | 28/08/2020 | Stellenbosch FC | - | Chippa United | 1:1 | ||||
| 10. Round | 02/09/2020 | Kaizer Chiefs | - | Chippa United | 1:0 |  |
Zimbabwe