1. Round | 03/08/2019 | Baroka FC | - | Cape Town City FC | 2:2 | ||||
1. Round | 10/08/2019 | Cape Town City FC | - | Stellenbosch FC | 1:0 | ||||
5. Round | 07/12/2019 | Cape Town City FC | - | Chippa United | 0:1 | ||||
5. Round | 20/12/2019 | BidVest Wits | - | Cape Town City FC | 2:0 | ||||
6. Round | 05/01/2020 | Cape Town City FC | - | Baroka FC | 1:0 | ||||
6. Round | 08/01/2020 | Cape Town City FC | - | AmaZulu FC | 2:2 | ||||
6. Round | 12/01/2020 | Kaizer Chiefs | - | Cape Town City FC | 3:0 | ||||
6. Round | 31/01/2020 | Maritzburg United | - | Cape Town City FC | 1:1 | ||||
8. Round | 08/03/2020 | Cape Town City FC | - | Bloemfontein Celtic | 2:0 |