| 1. Round | 05/08/2018 | Bloemfontein Celtic | - | Chippa United | 2:0 |  |
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| 1. Round | 08/08/2018 | Chippa United | - | Orlando Pirates | 0:1 | |
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| 1. Round | 18/08/2018 | Chippa United | - | Black Leopards | 2:2 | |
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| 1. Round | 29/08/2018 | SuperSport United | - | Chippa United | 2:1 | |
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| 2. Round | 22/09/2018 | Golden Arrows | - | Chippa United | 0:0 | ||||
| 3. Round | 03/10/2018 | Chippa United | - | Free State Stars | 1:0 | ||||
| 3. Round | 06/10/2018 | Highlands Park | - | Chippa United | 2:1 | ||||
| 3. Round | 27/10/2018 | Chippa United | - | Mamelodi Sundowns | 0:1 | ||||
| 5. Round | 11/12/2018 | Cape Town City FC | - | Chippa United | 1:1 | ||||
| 5. Round | 14/12/2018 | Chippa United | - | Polokwane City FC | 2:2 | ||||
| 5. Round | 21/12/2018 | BidVest Wits | - | Chippa United | 2:0 | ||||
| 6. Round | 04/01/2019 | Chippa United | - | Bloemfontein Celtic | 0:1 | ||||
| 6. Round | 08/01/2019 | Orlando Pirates | - | Chippa United | 4:2 |
South Africa