Head to Head
| 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 |
Home History
| South Africa Premier | 2020/09/05 13:30 | Orlando Pirates v Stellenbosch FC | W | 1-0 |
| South Africa Premier | 2020/09/02 16:00 | Maritzburg Utd v Orlando Pirates | W | 0-1 |
| South Africa Premier | 2020/08/29 11:30 | Orlando Pirates v Supersport United | W | 2-1 |
| South Africa Premier | 2020/08/23 13:30 | Cape Town City v Orlando Pirates | L | 1-0 |
| South Africa Premier | 2020/08/18 16:00 | Orlando Pirates v Baroka FC | D | 1-1 |
| South Africa Premier | 2020/08/15 16:00 | Orlando Pirates v Bidvest Wits | D | 0-0 |
| South Africa Premier | 2020/08/11 16:00 | Mamelodi Sundowns v Orlando Pirates | D | 0-0 |
| South Africa Premier | 2020/03/07 16:00 | Golden Arrows v Orlando Pirates | D | 0-0 |
Away History
| South Africa Premier | 2020/09/05 13:30 | Cape Town City v Supersport United | W | 1-0 |
| South Africa Premier | 2020/09/02 16:00 | Highlands Park v Cape Town City | L | 1-0 |
| South Africa Premier | 2020/08/29 16:00 | Golden Arrows v Cape Town City | W | 1-4 |
| South Africa Premier | 2020/08/23 13:30 | Cape Town City v Orlando Pirates | W | 1-0 |
| South Africa Premier | 2020/08/20 16:00 | Stellenbosch FC v Cape Town City | L | 1-0 |
| South Africa Premier | 2020/08/17 16:00 | Mamelodi Sundowns v Cape Town City | W | 2-3 |
| South Africa Premier | 2020/08/14 13:30 | Chippa United v Cape Town City | W | 0-1 |
| South Africa Premier | 2020/03/08 13:30 | Cape Town City v Bloem Celtic | W | 2-0 |