| 1. Round | 03/08/2019 | Orlando Pirates | - | Bloemfontein Celtic | 3:1 | ||||
| 1. Round | 14/08/2019 | SuperSport United | - | Orlando Pirates | 3:0 | ||||
| 1. Round | 28/08/2019 | Orlando Pirates | - | Golden Arrows | 0:0 | ||||
| 2. Round | 14/09/2019 | Orlando Pirates | - | Chippa United | 2:1 | ||||
| 2. Round | 21/09/2019 | BidVest Wits | - | Orlando Pirates | 4:3 |  |
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| 2. Round | 28/09/2019 | Orlando Pirates | - | Cape Town City FC | 3:3 |  |
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| 5. Round | 21/12/2019 | Orlando Pirates | - | Black Leopards | 3:1 |
South Africa