6. Round | 05/01/2019 | SuperSport United | - | Cape Town City FC | 0:1 | ||||
6. Round | 16/01/2019 | Cape Town City FC | - | Free State Stars | 5:0 | ||||
6. Round | 30/01/2019 | Kaizer Chiefs | - | Cape Town City FC | 0:1 | ||||
7. Round | 09/02/2019 | AmaZulu FC | - | Cape Town City FC | 1:0 | ||||
7. Round | 23/02/2019 | Cape Town City FC | - | Maritzburg United | 3:2 | ||||
7. Round | 27/02/2019 | Mamelodi Sundowns | - | Cape Town City FC | 3:2 | ||||
8. Round | 02/03/2019 | BidVest Wits | - | Cape Town City FC | 2:3 | ||||
8. Round | 05/03/2019 | Cape Town City FC | - | Mamelodi Sundowns | 2:1 | ||||
8. Round | 15/03/2019 | Cape Town City FC | - | Polokwane City FC | 0:0 | ||||
9. Round | 06/04/2019 | Golden Arrows | - | Cape Town City FC | 1:0 | ||||
9. Round | 14/04/2019 | Bloemfontein Celtic | - | Cape Town City FC | 0:3 dec. | ||||
9. Round | 23/04/2019 | Cape Town City FC | - | Highlands Park | 1:1 | ||||
10. Round | 11/05/2019 | Black Leopards | - | Cape Town City FC | 1:0 |