[4] Highlands Park 0-1 Orlando Pirates [10] 2019-10-29 17:30
Stadium: Makhulong Stadium Round: 1
Referee: Abongile Tom Home Manager: Owen Da Gama Away Manager: Rulani Mokwena
Head to Head
| South Africa Supa 8 Cup | 2019/08/17 16:00 | Orlando Pirates v Highlands Park | W | 0-1 |
| South Africa Premier | 2019/01/05 18:15 | Highlands Park v Orlando Pirates | D | 2-2 |
| South Africa Premier | 2018/08/04 18:15 | Orlando Pirates v Highlands Park | D | 1-1 |
| South Africa Premier | 2017/04/15 18:15 | Highlands Park v Orlando Pirates | D | 0-0 |
| South Africa Premier | 2016/12/03 18:15 | Orlando Pirates v Highlands Park | D | 2-2 |
| South Africa League Cup | 2016/11/05 18:30 | Orlando Pirates v Highlands Park | L | 2-1 |
Home History
| South Africa Premier | 2019/10/26 18:15 | Highlands Park v Chippa United | W | 2-0 |
| South Africa Premier | 2019/10/23 17:30 | Mamelodi Sundowns v Highlands Park | L | 1-0 |
| South Africa League Cup | 2019/10/20 13:00 | Highlands Park v Black Leopards | W | 6-5 |
| South Africa Supa 8 Cup | 2019/10/05 16:00 | Highlands Park v Supersport United | L | 0-1 |
| South Africa Premier | 2019/09/29 13:00 | Highlands Park v Polokwane City | W | 2-0 |
| South Africa Premier | 2019/09/22 13:00 | Baroka FC v Highlands Park | W | 1-2 |
| South Africa Supa 8 Cup | 2019/09/17 17:30 | Highlands Park v Polokwane City | W | 4-3 |
| South Africa Supa 8 Cup | 2019/08/31 13:00 | Polokwane City v Highlands Park | D | 0-0 |
Away History
| South Africa Premier | 2019/10/26 13:30 | Stellenbosch FC v Orlando Pirates | L | 1-0 |
| South Africa League Cup | 2019/10/19 16:00 | Orlando Pirates v Stellenbosch FC | W | 1-0 |
| South Africa Premier | 2019/09/28 13:00 | Orlando Pirates v Cape Town City | D | 3-3 |
| 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 |