| 1. Ronde | 08.08.2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
| 1. Ronde | 15.08.2018 | Orlando Pirates | - | BidVest Wits | 0:1 | ||||
| 1. Ronde | 19.08.2018 | Bloemfontein Celtic | - | Orlando Pirates | 1:0 | ||||
| 1. Ronde | 28.08.2018 | Black Leopards | - | Orlando Pirates | 1:2 |  |
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| 2. Ronde | 15.09.2018 | Orlando Pirates | - | SuperSport United | 3:1 | ||||
| 2. Ronde | 19.09.2018 | Orlando Pirates | - | Cape Town City FC | 2:2 | ||||
| 2. Ronde | 22.09.2018 | Baroka FC | - | Orlando Pirates | 1:2 | |
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| 3. Ronde | 03.10.2018 | Orlando Pirates | - | Golden Arrows | 0:0 | ||||
| 3. Ronde | 27.10.2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
| 4. Ronde | 10.11.2018 | Mamelodi Sundowns | - | Orlando Pirates | 0:0 | ||||
| 5. Ronde | 01.12.2018 | Orlando Pirates | - | Maritzburg United | 0:0 | ||||
| 5. Ronde | 11.12.2018 | Free State Stars | - | Orlando Pirates | 1:3 | ||||
| 6. Ronde | 05.01.2019 | Highlands Park | - | Orlando Pirates | 2:2 | ||||
| 6. Ronde | 08.01.2019 | Orlando Pirates | - | Chippa United | 4:2 | |
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| 9. Ronde | 01.04.2019 | Orlando Pirates | - | Mamelodi Sundowns | 0:0 |
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