| 1. Round | 04/08/2019 | Golden Arrows | - | Maritzburg United | 1:0 | ||||
| 1. Round | 09/08/2019 | Maritzburg United | - | Highlands Park | 1:1 | ||||
| 1. Round | 28/08/2019 | Maritzburg United | - | Black Leopards | 0:1 | ||||
| 2. Round | 21/09/2019 | Mamelodi Sundowns | - | Maritzburg United | 2:1 | ||||
| 2. Round | 27/09/2019 | Maritzburg United | - | Chippa United | 1:0 | ||||
| 6. Round | 26/01/2020 | Baroka FC | - | Maritzburg United | 2:1 | ||||
| 6. Round | 31/01/2020 | Maritzburg United | - | Cape Town City FC | 1:1 | ||||
| 7. Round | 12/02/2020 | BidVest Wits | - | Maritzburg United | 0:1 | ||||
| 7. Round | 15/02/2020 | Kaizer Chiefs | - | Maritzburg United | 1:2 | ||||
| 7. Round | 28/02/2020 | Maritzburg United | - | Stellenbosch FC | 3:0 | ||||
| 8. Round | 06/03/2020 | Maritzburg United | - | Polokwane City FC | 1:0 |  |
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| 9. Round | 16/08/2020 | Black Leopards | - | Maritzburg United | 3:2 | ||||
| 9. Round | 21/08/2020 | Maritzburg United | - | Mamelodi Sundowns | 2:2 | ||||
| 9. Round | 24/08/2020 | Maritzburg United | - | BidVest Wits | 0:0 | ||||
| 9. Round | 29/08/2020 | Highlands Park | - | Maritzburg United | 1:1 | |
South Africa