| 9. Round | 24/10/2023 | AmaZulu FC | - | Orlando Pirates | 0:0 | ||||
| 10. Round | 27/10/2023 | Orlando Pirates | - | Polokwane City FC | 1:1 | ||||
| 6. Round | 01/11/2023 | Cape Town Spurs | - | Orlando Pirates | 2:1 | ||||
| 11. Round | 07/11/2023 | Orlando Pirates | - | Sekhukhune United | 1:0 | ||||
| 12. Round | 11/11/2023 | Kaizer Chiefs | - | Orlando Pirates | 0:1 | ||||
| 13. Round | 25/11/2023 | Richards Bay FC | - | Orlando Pirates | 0:0 | ||||
| 4. Round | 05/12/2023 | Orlando Pirates | - | Moroka Swallows | 2:0 |  |
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| 14. Round | 09/12/2023 | Orlando Pirates | - | TS Galaxy | 1:0 | ||||
| 8. Round | 17/12/2023 | Golden Arrows | - | Orlando Pirates | 1:2 | ||||
| 15. Round | 23/12/2023 | SuperSport United | - | Orlando Pirates | 3:1 | |
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| 16. Round | 29/12/2023 | Orlando Pirates | - | Stellenbosch FC | 2:3 | ||||
| 26. Round | 28/04/2024 | Royal AM | - | Orlando Pirates | 0:4 |
South Africa