| 1. Round | 04/08/2019 | Highlands Park | - | Kaizer Chiefs | 2:3 | ||||
| 1. Round | 09/08/2019 | Maritzburg United | - | Highlands Park | 1:1 | ||||
| 1. Round | 24/08/2019 | Black Leopards | - | Highlands Park | 1:1 |  |
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| 1. Round | 27/08/2019 | Highlands Park | - | AmaZulu FC | 2:1 | ||||
| 2. Round | 22/09/2019 | Baroka FC | - | Highlands Park | 1:2 | ||||
| 2. Round | 29/09/2019 | Highlands Park | - | Polokwane City FC | 2:0 |  |
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| 4. Round | 26/11/2019 | Highlands Park | - | BidVest Wits | 1:1 | ||||
| 4. Round | 30/11/2019 | Cape Town City FC | - | Highlands Park | 0:0 | ||||
| 5. Round | 06/12/2019 | SuperSport United | - | Highlands Park | 2:0 | ||||
| 5. Round | 21/12/2019 | Highlands Park | - | Golden Arrows | 2:0 | ||||
| 6. Round | 05/01/2020 | Highlands Park | - | Black Leopards | 2:1 | ||||
| 6. Round | 08/01/2020 | Kaizer Chiefs | - | Highlands Park | 3:0 | |
South Africa