| Saturday, 12 October 2019 |
Highlands Park FC vs Black Leopards |
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1 - 0 |
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| Sunday, 6 October 2019 |
Golden Arrows vs Highlands Park FC |
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0 - 4 |
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| Saturday, 28 September 2019 |
Highlands Park FC vs Chippa United |
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1 - 1 |
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| Saturday, 14 September 2019 |
Highlands Park FC vs Stellenbosch FC |
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3 - 1 |
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| Saturday, 7 September 2019 |
Highlands Park FC vs Orlando Pirates |
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| Sunday, 25 August 2019 |
Highlands Park FC vs Polokwane City |
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3 - 1 |
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| Sunday, 18 August 2019 |
Kaizer Chiefs vs Highlands Park FC |
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2 - 3 |
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| Sunday, 11 August 2019 |
Highlands Park FC vs Baroka FC |
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0 - 3 |
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