1. Round | 03/08/2019 | Chippa United | - | Stellenbosch FC | 0:0 | ||||
1. Round | 10/08/2019 | Cape Town City FC | - | Stellenbosch FC | 1:0 | ||||
3. Round | 02/10/2019 | Polokwane City FC | - | Stellenbosch FC | 0:2 | ||||
4. Round | 09/11/2019 | Stellenbosch FC | - | Highlands Park | 0:0 | ||||
4. Round | 30/11/2019 | SuperSport United | - | Stellenbosch FC | 1:1 | ||||
5. Round | 11/12/2019 | Mamelodi Sundowns | - | Stellenbosch FC | 3:1 |