[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
| Sør-Afrika - Supa 8 Cup | 2019/08/17 16:00 | Orlando Pirates v Highlands Park | W | 0-1 |
| Sør-Afrika - Premier | 2019/01/05 18:15 | Highlands Park v Orlando Pirates | D | 2-2 |
| Sør-Afrika - Premier | 2018/08/04 18:15 | Orlando Pirates v Highlands Park | D | 1-1 |
| Sør-Afrika - Premier | 2017/04/15 18:15 | Highlands Park v Orlando Pirates | D | 0-0 |
| Sør-Afrika - Premier | 2016/12/03 18:15 | Orlando Pirates v Highlands Park | D | 2-2 |
| Sør-Afrika - League Cup | 2016/11/05 18:30 | Orlando Pirates v Highlands Park | L | 2-1 |