| 1. Round | 03/08/2019 | Chippa United | - | Stellenbosch FC | 0:0 | ||||
| 1. Round | 10/08/2019 | Cape Town City FC | - | Stellenbosch FC | 1:0 | ||||
| 1. Round | 25/08/2019 | Stellenbosch FC | - | Maritzburg United | 0:0 | ||||
| 1. Round | 28/08/2019 | BidVest Wits | - | Stellenbosch FC | 2:1 | ||||
| 2. Round | 15/09/2019 | Bloemfontein Celtic | - | Stellenbosch FC | 2:1 | ||||
| 4. Round | 06/11/2019 | AmaZulu FC | - | Stellenbosch FC | 2:0 | ||||
| 4. Round | 27/11/2019 | Stellenbosch FC | - | Kaizer Chiefs | 0:4 | ||||
| 5. Round | 21/12/2019 | Baroka FC | - | Stellenbosch FC | 0:1 | ||||
| 6. Round | 04/01/2020 | Stellenbosch FC | - | BidVest Wits | 0:2 | ||||
| 6. Round | 07/01/2020 | Stellenbosch FC | - | Bloemfontein Celtic | 1:2 | ||||
| 7. Round | 28/02/2020 | Maritzburg United | - | Stellenbosch FC | 3:0 | ||||
| 10. Round | 02/09/2020 | Stellenbosch FC | - | AmaZulu FC | 1:1 |
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