Highlands Park 1-0 Cape Town City 2020-09-02 16:00
Stadium: Makhulong Stadium Round: 1
Referee: Tshepiso Mkhwanazi Home Manager: Owen Da Gama Away Manager: Jan Olde Riekerink
Head to Head
| South Africa Premier | 2019/11/30 16:00 | Cape Town City v Highlands Park | D | 0-0 |
| South Africa Premier | 2019/04/23 17:30 | Cape Town City v Highlands Park | D | 1-1 |
| South Africa Cup | 2019/02/15 18:00 | Cape Town City v Highlands Park | L | 3-0 |
| South Africa Premier | 2018/12/01 13:30 | Highlands Park v Cape Town City | W | 2-0 |
| South Africa Premier | 2017/02/07 17:30 | Cape Town City v Highlands Park | L | 3-0 |
| South Africa Premier | 2016/09/27 17:30 | Highlands Park v Cape Town City | D | 1-1 |