| 4. Round | 09/11/2018 | Maritzburg United | - | Highlands Park | 2:2 | ||||
| 4. Round | 27/11/2018 | Highlands Park | - | AmaZulu FC | 1:2 | ||||
| 5. Round | 01/12/2018 | Highlands Park | - | Cape Town City FC | 2:0 |  |
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| 5. Round | 11/12/2018 | Polokwane City FC | - | Highlands Park | 2:2 | ||||
| 6. Round | 05/01/2019 | Highlands Park | - | Orlando Pirates | 2:2 | ||||
| 6. Round | 12/01/2019 | AmaZulu FC | - | Highlands Park | 0:0 | ||||
| 6. Round | 22/01/2019 | Highlands Park | - | Mamelodi Sundowns | 1:2 | ||||
| 7. Round | 02/02/2019 | Golden Arrows | - | Highlands Park | 2:1 | ||||
| 8. Round | 02/03/2019 | Kaizer Chiefs | - | Highlands Park | 3:2 | ||||
| 8. Round | 09/03/2019 | Highlands Park | - | Baroka FC | 2:1 | ||||
| 9. Round | 23/04/2019 | Cape Town City FC | - | Highlands Park | 1:1 | |
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| 9. Round | 27/04/2019 | Highlands Park | - | Polokwane City FC | 0:2 | ||||
| 10. Round | 04/05/2019 | Highlands Park | - | Bloemfontein Celtic | 1:0 | |
Zimbabwe