[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 |
| South Africa Premier | 2017/04/25 17:30 | Cape Town City v Kaizer Chiefs | W | 3-2 |
| South Africa Premier | 2016/11/29 17:30 | Kaizer Chiefs v Cape Town City | D | 1-1 |
| South Africa Supa 8 Cup | 2016/08/26 18:00 | Cape Town City v Kaizer Chiefs | W | 1-0 |