[12] Cape Town City 0-1 Chippa United [16] 2019-12-07 16:00
Stadium: Cape Town Stadium Round: 1
Home Manager: Jan Olde Riekerink Away Manager: Norman Mapeza
Head to Head
| South Africa Premier | 2019/04/26 18:00 | Chippa United v Cape Town City | W | 0-2 |
| South Africa Premier | 2018/12/11 17:30 | Cape Town City v Chippa United | D | 1-1 |
| South Africa Premier | 2018/03/02 18:00 | Cape Town City v Chippa United | W | 2-0 |
| South Africa Premier | 2017/10/22 13:30 | Chippa United v Cape Town City | L | 2-1 |
| South Africa Premier | 2017/04/03 17:30 | Cape Town City v Chippa United | W | 4-1 |
| South Africa Premier | 2016/11/19 13:30 | Chippa United v Cape Town City | W | 1-2 |
Home History
| South Africa Premier | 2019/11/30 16:00 | Cape Town City v Highlands Park | D | 0-0 |
| 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 |
Away History
| South Africa Premier | 2019/12/01 13:30 | Chippa United v Baroka FC | D | 0-0 |
| South Africa Premier | 2019/11/27 17:30 | Chippa United v Black Leopards | W | 3-0 |
| South Africa Premier | 2019/11/09 18:15 | Amazulu v Chippa United | W | 0-2 |
| South Africa Premier | 2019/11/06 17:30 | Chippa United v Kaizer Chiefs | L | 0-2 |
| South Africa League Cup | 2019/11/03 13:00 | Chippa United v Mamelodi Sundowns | L | 5-6 |
| South Africa Premier | 2019/10/26 18:15 | Highlands Park v Chippa United | L | 2-0 |
| South Africa League Cup | 2019/10/22 17:30 | Chippa United v Bloem Celtic | W | 1-0 |
| South Africa Premier | 2019/10/01 17:30 | Chippa United v Bidvest Wits | L | 0-1 |