1. Round | 05/08/2023 | Stellenbosch FC | - | Orlando Pirates | 1:0 | ||||
3. Round | 15/08/2023 | Chippa United | - | Orlando Pirates | 1:1 | ||||
11. Round | 07/11/2023 | Orlando Pirates | - | Sekhukhune United | 1:0 | ||||
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 | ||||
27. Round | 01/05/2024 | Cape Town City FC | - | Orlando Pirates | 0:2 |