[11] Cape Town City 0-0 Highlands Park [6] 2019-11-30 16:00
Stadium: Cape Town Stadium Round: 1
Referee: Masixole Bambiso Home Manager: Jan Olde Riekerink Away Manager: Owen Da Gama
Head to Head
| 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 | W | 3-0 |
| South Africa Premier | 2018/12/01 13:30 | Highlands Park v Cape Town City | L | 2-0 |
| South Africa Premier | 2017/02/07 17:30 | Cape Town City v Highlands Park | W | 3-0 |
| South Africa Premier | 2016/09/27 17:30 | Highlands Park v Cape Town City | D | 1-1 |
Home History
| South Africa Premier | 2019/11/27 17:30 | Bloem Celtic v Cape Town City | D | 0-0 |
| South Africa Premier | 2019/11/10 13:30 | Black Leopards v Cape Town City | L | 2-1 |
| South Africa Premier | 2019/11/06 17:30 | Cape Town City v Polokwane City | W | 5-3 |
| South Africa Premier | 2019/10/25 18:00 | Cape Town City v Maritzburg Utd | L | 0-1 |
| South Africa League Cup | 2019/10/19 13:00 | Cape Town City v Kaizer Chiefs | L | 3-5 |
| South Africa Premier | 2019/10/01 17:30 | Amazulu v Cape Town City | L | 2-1 |
| South Africa Premier | 2019/09/28 13:00 | Orlando Pirates v Cape Town City | D | 3-3 |
| South Africa Premier | 2019/09/22 13:00 | Cape Town City v Golden Arrows | D | 1-1 |
Away History
| South Africa Premier | 2019/11/26 17:30 | Highlands Park v Bidvest Wits | D | 1-1 |
| South Africa Premier | 2019/11/09 13:30 | Stellenbosch FC v Highlands Park | D | 0-0 |
| South Africa Premier | 2019/11/05 17:30 | Bloem Celtic v Highlands Park | L | 3-1 |
| South Africa League Cup | 2019/11/01 18:00 | Maritzburg Utd v Highlands Park | L | 5-4 |
| South Africa Premier | 2019/10/29 17:30 | Highlands Park v Orlando Pirates | L | 0-1 |
| South Africa Premier | 2019/10/26 18:15 | Highlands Park v Chippa United | W | 2-0 |
| South Africa Premier | 2019/10/23 17:30 | Mamelodi Sundowns v Highlands Park | L | 1-0 |
| South Africa League Cup | 2019/10/20 13:00 | Highlands Park v Black Leopards | W | 6-5 |