1. Round | 10/08/2019 | Cape Town City FC | - | Stellenbosch FC | 1:0 | ||||
1. Round | 20/08/2019 | Mamelodi Sundowns | - | Cape Town City FC | 1:1 | ||||
1. Round | 27/08/2019 | Cape Town City FC | - | Kaizer Chiefs | 1:2 | ||||
2. Round | 14/09/2019 | SuperSport United | - | Cape Town City FC | 3:3 | ||||
4. Round | 06/11/2019 | Cape Town City FC | - | Polokwane City FC | 5:3 | ||||
4. Round | 10/11/2019 | Black Leopards | - | Cape Town City FC | 2:1 | ||||
4. Round | 27/11/2019 | Bloemfontein Celtic | - | Cape Town City FC | 0:0 | ||||
4. Round | 30/11/2019 | Cape Town City FC | - | Highlands Park | 0:0 | ||||
5. Round | 20/12/2019 | BidVest Wits | - | Cape Town City FC | 2:0 |