| 1. Round | 08/08/2018 | Free State Stars | - | Maritzburg United | 2:1 |  |
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| 1. Round | 17/08/2018 | Maritzburg United | - | Kaizer Chiefs | 0:0 | ||||
| 2. Round | 15/09/2018 | Maritzburg United | - | BidVest Wits | 0:0 | ||||
| 2. Round | 23/09/2018 | Bloemfontein Celtic | - | Maritzburg United | 0:1 |  |
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| 3. Round | 02/10/2018 | AmaZulu FC | - | Maritzburg United | 0:0 | |
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| 3. Round | 05/10/2018 | Maritzburg United | - | Cape Town City FC | 0:0 | ||||
| 3. Round | 27/10/2018 | Polokwane City FC | - | Maritzburg United | 1:0 | ||||
| 4. Round | 09/11/2018 | Maritzburg United | - | Highlands Park | 2:2 | ||||
| 5. Round | 01/12/2018 | Orlando Pirates | - | Maritzburg United | 0:0 | ||||
| 5. Round | 12/12/2018 | Maritzburg United | - | Black Leopards | 1:1 | ||||
| 5. Round | 15/12/2018 | SuperSport United | - | Maritzburg United | 1:0 | ||||
| 5. Round | 22/12/2018 | Maritzburg United | - | Baroka FC | 0:1 | ||||
| 6. Round | 06/01/2019 | Golden Arrows | - | Maritzburg United | 2:0 | ||||
| 6. Round | 09/01/2019 | Maritzburg United | - | Free State Stars | 1:2 | |
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| 6. Round | 16/01/2019 | Mamelodi Sundowns | - | Maritzburg United | 1:0 | ||||
| 6. Round | 19/01/2019 | Chippa United | - | Maritzburg United | 2:0 |
South Africa