[5] Cape Town City 1-2 Kaizer Chiefs [10] 2021-01-16 15:00
Stadium: Cape Town Stadium Round: 1
Referee: Thokozani Mkhize Home Manager: Jan Olde Riekerink Away Manager: Gavin Hunt
Head to Head
| South Africa Premier | 2020/01/12 13:30 | Kaizer Chiefs v Cape Town City | L | 3-0 |
| South Africa League Cup | 2019/10/19 13:00 | Cape Town City v Kaizer Chiefs | L | 3-5 |
| South Africa Premier | 2019/08/27 17:30 | Cape Town City v Kaizer Chiefs | L | 1-2 |
| South Africa Cup | 2019/03/31 13:00 | Kaizer Chiefs v Cape Town City | L | 2-0 |
| South Africa Premier | 2019/01/30 17:30 | Kaizer Chiefs v Cape Town City | W | 0-1 |
| South Africa Premier | 2018/09/15 13:00 | Cape Town City v Kaizer Chiefs | L | 1-4 |
| South Africa Premier | 2018/02/17 18:15 | Kaizer Chiefs v Cape Town City | L | 1-0 |
| South Africa Premier | 2017/09/13 17:30 | Cape Town City v Kaizer Chiefs | L | 0-2 |
Home History
| South Africa Premier | 2021/01/09 15:00 | Tshakhuma Tsha Madzivhadila v Cape Town City | D | 2-2 |
| South Africa Premier | 2021/01/05 15:00 | Moroka Swallows v Cape Town City | L | 3-2 |
| South Africa Premier | 2020/12/19 16:00 | Cape Town City v TS Galaxy | W | 3-2 |
| South Africa Premier | 2020/12/15 17:30 | Stellenbosch FC v Cape Town City | W | 1-2 |
| South Africa Premier | 2020/12/05 13:30 | Cape Town City v Orlando Pirates | D | 2-2 |
| South Africa Premier | 2020/11/28 18:15 | Amazulu v Cape Town City | D | 1-1 |
| South Africa Premier | 2020/11/22 13:30 | Cape Town City v Bloem Celtic | W | 4-2 |
| South Africa Premier | 2020/11/04 17:30 | Cape Town City v Mamelodi Sundowns | L | 0-2 |
Away History
| South Africa Premier | 2021/01/13 13:00 | Amazulu v Kaizer Chiefs | W | 0-1 |
| South Africa Premier | 2021/01/09 15:00 | Kaizer Chiefs v Maritzburg Utd | L | 0-2 |
| CAF Champions League | 2021/01/05 15:00 | Primeiro de Agosto v Kaizer Chiefs | W | 0-1 |
| CAF Champions League | 2020/12/23 16:00 | Kaizer Chiefs v Primeiro de Agosto | D | 0-0 |
| South Africa Premier | 2020/12/19 16:00 | Kaizer Chiefs v Bloem Celtic | D | 1-1 |
| South Africa Premier | 2020/12/15 17:30 | Supersport United v Kaizer Chiefs | L | 2-1 |
| South Africa Premier | 2020/12/09 17:30 | Kaizer Chiefs v Black Leopards | D | 2-2 |
| CAF Champions League | 2020/12/05 16:00 | Kaizer Chiefs v PWD de Bamenda | D | 0-0 |