1. Round | 04/08/2018 | Orlando Pirates | - | Highlands Park | 1:1 | ||||
1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
1. Round | 15/08/2018 | Orlando Pirates | - | BidVest Wits | 0:1 | ||||
1. Round | 28/08/2018 | Black Leopards | - | Orlando Pirates | 1:2 | ||||
2. Round | 15/09/2018 | Orlando Pirates | - | SuperSport United | 3:1 | ||||
2. Round | 19/09/2018 | Orlando Pirates | - | Cape Town City FC | 2:2 | ||||
2. Round | 22/09/2018 | Baroka FC | - | Orlando Pirates | 1:2 | ||||
3. Round | 03/10/2018 | Orlando Pirates | - | Golden Arrows | 0:0 | ||||
3. Round | 27/10/2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
4. Round | 06/11/2018 | Polokwane City FC | - | Orlando Pirates | 1:2 | ||||
5. Round | 01/12/2018 | Orlando Pirates | - | Maritzburg United | 0:0 | ||||
5. Round | 11/12/2018 | Free State Stars | - | Orlando Pirates | 1:3 | ||||
6. Round | 22/01/2019 | Orlando Pirates | - | Baroka FC | 1:1 |