[10] Orlando Pirates 3-3 Cape Town City [11] 2019-09-28 13:00
Stadium: Orlando Stadium Round: 1
Home Manager: Rulani Mokwena Away Manager: Benni McCarthy
Head to Head
| 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 |
Home History
| South Africa Premier | 2019/09/21 18:15 | Bidvest Wits v Orlando Pirates | L | 4-3 |
| South Africa Premier | 2019/09/14 13:00 | Orlando Pirates v Chippa United | W | 2-1 |
| South Africa Premier | 2019/08/28 17:30 | Orlando Pirates v Golden Arrows | D | 0-0 |
| CAF Champions League | 2019/08/24 19:00 | Orlando Pirates v Green Eagles | D | 1-1 |
| South Africa Premier | 2019/08/20 17:30 | Amazulu v Orlando Pirates | D | 0-0 |
| South Africa Supa 8 Cup | 2019/08/17 16:00 | Orlando Pirates v Highlands Park | L | 0-1 |
| South Africa Premier | 2019/08/14 17:30 | Supersport United v Orlando Pirates | L | 3-0 |
| CAF Champions League | 2019/08/10 13:00 | Green Eagles v Orlando Pirates | L | 1-0 |
Away History
| South Africa Premier | 2019/09/22 13:00 | Cape Town City v Golden Arrows | D | 1-1 |
| South Africa Premier | 2019/09/14 18:15 | Supersport United v Cape Town City | D | 3-3 |
| South Africa Premier | 2019/08/27 17:30 | Cape Town City v Kaizer Chiefs | L | 1-2 |
| South Africa Premier | 2019/08/20 17:30 | Mamelodi Sundowns v Cape Town City | D | 1-1 |
| South Africa Supa 8 Cup | 2019/08/17 13:00 | Cape Town City v Polokwane City | L | 0-2 |
| South Africa Premier | 2019/08/10 16:00 | Cape Town City v Stellenbosch FC | W | 1-0 |
| South Africa Premier | 2019/08/03 13:00 | Baroka FC v Cape Town City | D | 2-2 |
| South Africa Premier | 2019/05/11 13:00 | Black Leopards v Cape Town City | L | 1-0 |