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 |
Home History
| South Africa Premier | 2025/02/01 13:30 | Orlando Pirates v Kaizer Chiefs | W | 1-0 |
| South Africa Cup | 2025/01/26 13:00 | Richards Bay FC v Orlando Pirates | W | 1-3 |
| CAF Champions League | 2025/01/18 16:00 | Al Ahly Cairo v Orlando Pirates | W | 1-2 |
| CAF Champions League | 2025/01/12 13:00 | Orlando Pirates v CR Belouizdad | W | 2-1 |
| South Africa Premier | 2025/01/08 17:30 | Cape Town City v Orlando Pirates | L | 1-0 |
| CAF Champions League | 2025/01/04 16:00 | Orlando Pirates v Stade d'Abidjan | W | 3-0 |
| South Africa Premier | 2024/12/29 13:30 | Magesi FC v Orlando Pirates | W | 0-1 |
| South Africa Premier | 2024/12/24 13:00 | Orlando Pirates v Marumo Gallants | W | 8-1 |
Away History
| South Africa Premier | 2025/02/02 13:30 | TS Galaxy v Cape Town City | L | 2-0 |
| South Africa Cup | 2025/01/27 17:00 | Sekhukhune United FC v Cape Town City | L | 2-0 |
| South Africa Premier | 2025/01/17 17:30 | Cape Town City v Richards Bay FC | W | 2-1 |
| South Africa Premier | 2025/01/11 13:30 | Marumo Gallants v Cape Town City | L | 1-0 |
| South Africa Premier | 2025/01/08 17:30 | Cape Town City v Orlando Pirates | W | 1-0 |
| South Africa Premier | 2025/01/05 15:45 | Cape Town City v Kaizer Chiefs | W | 1-0 |
| South Africa Premier | 2024/12/29 13:30 | Cape Town City v Amazulu | L | 0-1 |
| South Africa Premier | 2024/12/14 15:30 | Chippa United v Cape Town City | W | 0-1 |