1. Round | 19/08/2018 | Bloemfontein Celtic | - | Orlando Pirates | 1:0 | ||||
1. Round | 28/08/2018 | Black Leopards | - | Orlando Pirates | 1:2 | ||||
3. Round | 27/10/2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
4. Round | 06/11/2018 | Polokwane City FC | - | Orlando Pirates | 1:2 | ||||
4. Round | 10/11/2018 | Mamelodi Sundowns | - | Orlando Pirates | 0:0 | ||||
5. Round | 01/12/2018 | Orlando Pirates | - | Maritzburg United | 0:0 | ||||
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 | ||||
7. Round | 23/02/2019 | Orlando Pirates | - | AmaZulu FC | 4:1 | ||||
9. Round | 06/04/2019 | BidVest Wits | - | Orlando Pirates | 0:1 | ||||
9. Round | 10/04/2019 | Orlando Pirates | - | Black Leopards | 2:0 | ||||
9. Round | 13/04/2019 | Orlando Pirates | - | Free State Stars | 2:1 | ||||
9. Round | 24/04/2019 | Maritzburg United | - | Orlando Pirates | 0:1 | ||||
10. Round | 04/05/2019 | Cape Town City FC | - | Orlando Pirates | 2:2 | ||||
10. Round | 11/05/2019 | Orlando Pirates | - | Polokwane City FC | 3:0 |