1. Round | 29/08/2018 | Free State Stars | - | Cape Town City FC | 2:2 | ||||
2. Round | 15/09/2018 | Cape Town City FC | - | Kaizer Chiefs | 1:4 | ||||
2. Round | 19/09/2018 | Orlando Pirates | - | Cape Town City FC | 2:2 | ||||
3. Round | 02/10/2018 | Cape Town City FC | - | BidVest Wits | 0:2 | ||||
3. Round | 05/10/2018 | Maritzburg United | - | Cape Town City FC | 0:0 | ||||
6. Round | 05/01/2019 | SuperSport United | - | Cape Town City FC | 0:1 | ||||
6. Round | 12/01/2019 | Cape Town City FC | - | Baroka FC | 2:2 | ||||
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 | ||||
8. Round | 02/03/2019 | BidVest Wits | - | Cape Town City FC | 2:3 |