| 1. Jornada | 28.08.2018 | Black Leopards | - | Orlando Pirates | 1:2 | ||||
| 2. Jornada | 15.09.2018 | Orlando Pirates | - | SuperSport United | 3:1 | ||||
| 2. Jornada | 19.09.2018 | Orlando Pirates | - | Cape Town City FC | 2:2 | ||||
| 2. Jornada | 22.09.2018 | Baroka FC | - | Orlando Pirates | 1:2 | ||||
| 3. Jornada | 27.10.2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
| 4. Jornada | 06.11.2018 | Polokwane City FC | - | Orlando Pirates | 1:2 | ||||
| 4. Jornada | 10.11.2018 | Mamelodi Sundowns | - | Orlando Pirates | 0:0 | ||||
| 5. Jornada | 11.12.2018 | Free State Stars | - | Orlando Pirates | 1:3 |  |
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| 6. Jornada | 05.01.2019 | Highlands Park | - | Orlando Pirates | 2:2 | ||||
| 6. Jornada | 22.01.2019 | Orlando Pirates | - | Baroka FC | 1:1 |
Sudáfrica