1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | ||||
3. Round | 27/10/2018 | Orlando Pirates | - | Kaizer Chiefs | 2:1 | ||||
5. Round | 11/12/2018 | Free State Stars | - | Orlando Pirates | 1:3 | ||||
6. Round | 05/01/2019 | Highlands Park | - | Orlando Pirates | 2:2 | ||||
7. Round | 20/02/2019 | SuperSport United | - | Orlando Pirates | 1:0 |