[15] Chippa United 1-1 Highlands Park [9] 2019-03-17 13:30
Stadium: Nelson Mandela Bay Stadium Round: 1
Referee: Phillip Tinyani Home Manager: Clinton Larsen Away Manager: Owen Da Gama
Head to Head
| South Africa Premier | 2018/10/06 18:15 | Highlands Park v Chippa United | L | 2-1 |
| South Africa Premier | 2017/05/12 18:00 | Highlands Park v Chippa United | L | 1-0 |
| South Africa Premier | 2016/12/17 13:30 | Chippa United v Highlands Park | W | 2-0 |
| South Africa League Cup | 2016/10/21 18:00 | Highlands Park v Chippa United | L | 2-0 |
Home History
| South Africa Premier | 2019/03/10 13:30 | Black Leopards v Chippa United | L | 3-2 |
| South Africa Premier | 2019/03/03 13:30 | Chippa United v Supersport United | L | 0-1 |
| South Africa Premier | 2019/02/22 18:00 | Chippa United v Golden Arrows | D | 1-1 |
| South Africa Cup | 2019/02/16 13:00 | Chippa United v Tshakhuma Tsha Madzivhadila | W | 2-0 |
| South Africa Premier | 2019/02/09 16:00 | Free State Stars v Chippa United | W | 0-2 |
| South Africa Premier | 2019/02/03 13:30 | Baroka FC v Chippa United | D | 1-1 |
| South Africa Cup | 2019/01/26 13:00 | Chippa United v Mamelodi Sundowns | W | 2-1 |
| South Africa Premier | 2019/01/19 13:30 | Chippa United v Maritzburg Utd | W | 2-0 |
Away History
| South Africa Premier | 2019/03/09 13:30 | Highlands Park v Baroka FC | W | 2-1 |
| South Africa Premier | 2019/03/02 16:00 | Kaizer Chiefs v Highlands Park | L | 3-2 |
| South Africa Premier | 2019/02/24 13:30 | Black Leopards v Highlands Park | D | 0-0 |
| South Africa Cup | 2019/02/15 18:00 | Cape Town City v Highlands Park | L | 3-0 |
| South Africa Premier | 2019/02/09 13:30 | Highlands Park v Bidvest Wits | W | 2-1 |
| South Africa Premier | 2019/02/02 13:30 | Golden Arrows v Highlands Park | L | 2-1 |
| South Africa Cup | 2019/01/25 18:00 | Amazulu v Highlands Park | W | 2-4 |
| South Africa Premier | 2019/01/22 17:30 | Highlands Park v Mamelodi Sundowns | L | 1-2 |