Head to Head
| South Africa Premier | 2024/05/01 13:00 | Cape Town City v Orlando Pirates | L | 0-2 |
| South Africa Premier | 2023/08/29 17:30 | Orlando Pirates v Cape Town City | L | 2-0 |
| South Africa Premier | 2023/04/22 13:00 | Orlando Pirates v Cape Town City | L | 2-1 |
| South Africa Premier | 2023/01/07 15:30 | Cape Town City v Orlando Pirates | W | 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 | L | 2-0 |
| South Africa Premier | 2020/12/05 13:30 | Cape Town City v Orlando Pirates | D | 2-2 |
Home History
| South Africa Supa 8 Cup | 2024/08/10 13:00 | Sekhukhune United FC v Cape Town City | W | 0-1 |
| South Africa Premier | 2024/05/25 13:00 | Mamelodi Sundowns v Cape Town City | W | 0-1 |
| South Africa Premier | 2024/05/18 13:00 | Cape Town City v Richards Bay FC | W | 3-1 |
| South Africa Premier | 2024/05/12 13:00 | Cape Town City v TS Galaxy | D | 1-1 |
| South Africa Premier | 2024/05/07 17:30 | Cape Town City v Moroka Swallows | W | 2-0 |
| South Africa Premier | 2024/05/01 13:00 | Cape Town City v Orlando Pirates | L | 0-2 |
| South Africa Premier | 2024/04/28 15:30 | Cape Town City v Golden Arrows | D | 1-1 |
| South Africa Premier | 2024/04/21 13:00 | Polokwane City v Cape Town City | D | 2-2 |
Away History
| CAF Champions League | 2024/08/23 17:30 | Orlando Pirates v CS-DFC | W | 4-0 |
| CAF Champions League | 2024/08/18 11:00 | CS-DFC v Orlando Pirates | D | 0-0 |
| South Africa Supa 8 Cup | 2024/08/03 16:00 | Orlando Pirates v Supersport United | W | 3-1 |
| World Club Friendlies | 2024/07/19 17:30 | Al Sadd v Orlando Pirates | L | 3-2 |
| World Club Friendlies | 2024/07/17 17:00 | Granada v Orlando Pirates | D | 1-1 |
| World Club Friendlies | 2024/07/15 19:00 | Sevilla v Orlando Pirates | W | 0-2 |
| World Club Friendlies | 2024/07/12 17:00 | Plymouth v Orlando Pirates | D | 2-2 |
| South Africa Cup | 2024/06/01 13:00 | Mamelodi Sundowns v Orlando Pirates | W | 1-2 |