| PSL | 03.04.17 | Cape Town City FC | - | Chippa United | 4:1 |  |
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| PSL | 22.10.17 | Chippa United | - | Cape Town City FC | 2:1 |  |
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| PSL | 02.03.18 | Cape Town City FC | - | Chippa United | 2:0 | ||||
| PSL | 11.12.18 | Cape Town City FC | - | Chippa United | 1:1 | ||||
| PSL | 26.04.19 | Chippa United | - | Cape Town City FC | 0:2 | ||||
| PSL | 07.12.19 | Cape Town City FC | - | Chippa United | 0:1 | ||||
| PSL | 14.08.20 | Chippa United | - | Cape Town City FC | 0:1 | ||||
| PSL | 24.10.20 | Cape Town City FC | - | Chippa United | 1:1 | ||||
| PSL | 03.03.21 | Chippa United | - | Cape Town City FC | 0:0 | ||||
| PSL | 03.11.21 | Cape Town City FC | - | Chippa United | 1:0 | ||||
| PSL | 04.05.22 | Chippa United | - | Cape Town City FC | 0:0 | ||||
| PSL | 25.10.22 | Cape Town City FC | - | Chippa United | 2:1 | |
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| PSL | 14.01.23 | Chippa United | - | Cape Town City FC | 1:1 | ||||
| PSL | 17.02.24 | Chippa United | - | Cape Town City FC | 1:1 | ||||
| PSL | 14.12.24 | Chippa United | - | Cape Town City FC | 0:1 | |
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