[7] Highlands Park 2-0 Chippa United [16] 2019-10-26 18:15
Stadium: Makhulong Stadium Round: 1
Home Manager: Owen Da Gama Away Manager: Norman Mapeza
Head to Head
| South Africa Premier | 2019/03/17 13:30 | Chippa United v Highlands Park | D | 1-1 |
| South Africa Premier | 2018/10/06 18:15 | Highlands Park v Chippa United | W | 2-1 |
| South Africa Premier | 2017/05/12 18:00 | Highlands Park v Chippa United | W | 1-0 |
| South Africa Premier | 2016/12/17 13:30 | Chippa United v Highlands Park | L | 2-0 |
| South Africa League Cup | 2016/10/21 18:00 | Highlands Park v Chippa United | W | 2-0 |