[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 |
Home History
| 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 |
| South Africa Premier | 2019/08/27 17:30 | Highlands Park v Amazulu | W | 2-1 |
Away History
| South Africa League Cup | 2019/10/22 17:30 | Chippa United v Bloem Celtic | W | 1-0 |
| South Africa Premier | 2019/10/01 17:30 | Chippa United v Bidvest Wits | L | 0-1 |
| South Africa Premier | 2019/09/27 18:00 | Maritzburg Utd v Chippa United | L | 1-0 |
| South Africa Premier | 2019/09/21 13:00 | Chippa United v Bloem Celtic | D | 0-0 |
| South Africa Premier | 2019/09/14 13:00 | Orlando Pirates v Chippa United | L | 2-1 |
| South Africa Premier | 2019/08/28 17:30 | Chippa United v Polokwane City | D | 0-0 |
| South Africa Premier | 2019/08/24 13:00 | Golden Arrows v Chippa United | L | 2-1 |
| South Africa Premier | 2019/08/14 17:30 | Chippa United v Mamelodi Sundowns | D | 1-1 |