| 6. Round | 08/01/2019 | Orlando Pirates | - | Chippa United | 4:2 | ||||
| 6. Round | 22/01/2019 | Orlando Pirates | - | Baroka FC | 1:1 | ||||
| 7. Round | 09/02/2019 | Kaizer Chiefs | - | Orlando Pirates | 1:1 |  |
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| 7. Round | 20/02/2019 | SuperSport United | - | Orlando Pirates | 1:0 | ||||
| 7. Round | 23/02/2019 | Orlando Pirates | - | AmaZulu FC | 4:1 | ||||
| 8. Round | 02/03/2019 | Golden Arrows | - | Orlando Pirates | 0:1 | ||||
| 8. Round | 05/03/2019 | Orlando Pirates | - | Bloemfontein Celtic | 1:1 | ||||
| 9. Round | 01/04/2019 | Orlando Pirates | - | Mamelodi Sundowns | 0:0 | |
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| 9. Round | 06/04/2019 | BidVest Wits | - | Orlando Pirates | 0:1 | |
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| 9. Round | 24/04/2019 | Maritzburg United | - | Orlando Pirates | 0:1 |
South Africa