| PSL | 02.03.19 | Kaizer Chiefs | - | Highlands Park | 3:2 |  |
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| PSL | 11.05.19 | SuperSport United | - | Highlands Park | 0:2 | ||||
| PSL | 23.10.19 | Mamelodi Sundowns | - | Highlands Park | 1:0 | ||||
| PSL | 01.02.20 | Highlands Park | - | Baroka FC | 1:0 | |
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| PSL | 14.08.20 | Highlands Park | - | Mamelodi Sundowns | 1:1 | |
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