Head to Head
| South Africa Premier | 2025/01/08 17:30 | Cape Town City v Orlando Pirates | L | 1-0 |
| South Africa Supa 8 Cup | 2024/08/31 13:00 | Orlando Pirates v Cape Town City | W | 2-0 |
| South Africa Supa 8 Cup | 2024/08/28 16:00 | Cape Town City v Orlando Pirates | D | 1-1 |
| South Africa Premier | 2024/05/01 13:00 | Cape Town City v Orlando Pirates | W | 0-2 |
| South Africa Premier | 2023/08/29 17:30 | Orlando Pirates v Cape Town City | W | 2-0 |
| South Africa Premier | 2023/04/22 13:00 | Orlando Pirates v Cape Town City | W | 2-1 |
| South Africa Premier | 2023/01/07 15:30 | Cape Town City v Orlando Pirates | L | 2-1 |
| South Africa Premier | 2022/03/02 15:30 | Orlando Pirates v Cape Town City | D | 0-0 |
| South Africa Premier | 2021/10/02 15:30 | Cape Town City v Orlando Pirates | D | 1-1 |
| South Africa Premier | 2021/02/09 15:00 | Orlando Pirates v Cape Town City | W | 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 | W | 1-0 |
| South Africa Premier | 2020/08/23 13:30 | Cape Town City v Orlando Pirates | L | 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 | L | 1-0 |
| South Africa Cup | 2018/03/14 17:30 | Cape Town City v Orlando Pirates | L | 1-0 |
| South Africa Premier | 2017/09/19 17:30 | Orlando Pirates v Cape Town City | W | 1-0 |
| South Africa Premier | 2017/02/18 18:15 | Cape Town City v Orlando Pirates | D | 2-2 |
| South Africa Premier | 2016/09/20 17:30 | Orlando Pirates v Cape Town City | D | 0-0 |