[11] Cape Town City 1-1 Orlando Pirates [5] 2021-10-02 15:30
Stadium: Cape Town Stadium Round: 1
Referee: Luxolo Badi Home Manager: Eric Tinkler Away Manager: Mandla Ncikazi
Head to Head
| South Africa Premier | 2021/02/09 15:00 | Orlando Pirates v Cape Town City | L | 2-0 |
| South Africa Premier | 2020/12/05 13:30 | Cape Town City v Orlando Pirates | D | 2-2 |
| South Africa Cup | 2020/10/17 16:00 | Orlando Pirates v Cape Town City | L | 1-0 |
| South Africa Premier | 2020/08/23 13:30 | Cape Town City v Orlando Pirates | W | 1-0 |
| South Africa Premier | 2019/09/28 13:00 | Orlando Pirates v Cape Town City | D | 3-3 |
| South Africa Premier | 2019/05/04 13:00 | Cape Town City v Orlando Pirates | D | 2-2 |
| South Africa Premier | 2018/09/19 17:30 | Orlando Pirates v Cape Town City | D | 2-2 |
| South Africa Premier | 2018/04/28 13:00 | Cape Town City v Orlando Pirates | W | 1-0 |
Home History
| South Africa Supa 8 Cup | 2021/09/29 16:00 | Moroka Swallows v Cape Town City | W | 0-4 |
| South Africa Premier | 2021/09/24 15:00 | Moroka Swallows v Cape Town City | D | 0-0 |
| South Africa Premier | 2021/09/18 15:00 | Cape Town City v Stellenbosch FC | L | 0-3 |
| South Africa Supa 8 Cup | 2021/08/29 13:00 | Cape Town City v Moroka Swallows | D | 0-0 |
| South Africa Premier | 2021/08/25 15:00 | Royal AM FC v Cape Town City | W | 1-2 |
| South Africa Premier | 2021/08/21 15:00 | Cape Town City v Supersport United | D | 0-0 |
| South Africa Supa 8 Cup | 2021/08/15 16:00 | Amazulu v Cape Town City | W | 1-2 |
| South Africa Premier | 2021/06/05 13:00 | Mamelodi Sundowns v Cape Town City | L | 3-0 |
Away History
| South Africa Premier | 2021/09/25 13:00 | Orlando Pirates v Mamelodi Sundowns | L | 0-2 |
| South Africa Premier | 2021/09/18 13:00 | Chippa United v Orlando Pirates | W | 1-3 |
| South Africa Premier | 2021/09/11 13:00 | Orlando Pirates v Moroka Swallows | W | 1-0 |
| South Africa Premier | 2021/08/24 15:00 | Marumo Gallants v Orlando Pirates | D | 0-0 |
| South Africa Premier | 2021/08/21 13:00 | Orlando Pirates v Stellenbosch FC | D | 2-2 |
| South Africa Supa 8 Cup | 2021/08/14 16:00 | Orlando Pirates v Moroka Swallows | L | 1-2 |
| South Africa Cup | 2021/08/01 15:00 | Kaizer Chiefs v Orlando Pirates | L | 4-3 |
| South Africa Premier | 2021/06/05 13:00 | Orlando Pirates v Tshakhuma Tsha Madzivhadila | D | 0-0 |