| PSL | 18.02.17 | Cape Town City FC | - | Orlando Pirates | 2:2 | ||||
| PSL | 19.09.17 | Orlando Pirates | - | Cape Town City FC | 1:0 | ||||
| PSL | 28.04.18 | Cape Town City FC | - | Orlando Pirates | 1:0 | ||||
| PSL | 04.05.19 | Cape Town City FC | - | Orlando Pirates | 2:2 | ||||
| PSL | 28.09.19 | Orlando Pirates | - | Cape Town City FC | 3:3 |  |
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| PSL | 23.08.20 | Cape Town City FC | - | Orlando Pirates | 1:0 | |
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| PSL | 05.12.20 | Cape Town City FC | - | Orlando Pirates | 2:2 | ||||
| PSL | 02.10.21 | Cape Town City FC | - | Orlando Pirates | 1:1 | |
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| PSL | 02.03.22 | Orlando Pirates | - | Cape Town City FC | 0:0 | ||||
| PSL | 07.01.23 | Cape Town City FC | - | Orlando Pirates | 2:1 | ||||
| PSL | 22.04.23 | Orlando Pirates | - | Cape Town City FC | 2:1 | ||||
| PSL | 29.08.23 | Orlando Pirates | - | Cape Town City FC | 2:0 | ||||
| PSL | 01.05.24 | Cape Town City FC | - | Orlando Pirates | 0:2 | ||||
| PSL | 08.01.25 | Cape Town City FC | - | Orlando Pirates | 1:0 |
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