1. Round | 03/08/2019 | Chippa United | - | Stellenbosch FC | 0:0 | ||||
2. Round | 15/09/2019 | Bloemfontein Celtic | - | Stellenbosch FC | 2:1 | ||||
2. Round | 21/09/2019 | Stellenbosch FC | - | Black Leopards | 2:2 | ||||
4. Round | 09/11/2019 | Stellenbosch FC | - | Highlands Park | 0:0 |