[8] Highlands Park 2-3 Kaizer Chiefs [8] 2019-08-04 13:00
Stadium: Makhulong Stadium Round: 1
Referee: Eugene Mdluli Home Manager: Owen Da Gama Away Manager: Ernst Middendorp
Head to Head
| Africa de Sud - Premier | 2019/03/02 16:00 | Kaizer Chiefs v Highlands Park | L | 3-2 |
| Africa de Sud - Premier | 2018/10/02 17:30 | Highlands Park v Kaizer Chiefs | D | 0-0 |
| Africa de Sud - Premier | 2017/02/18 16:00 | Kaizer Chiefs v Highlands Park | L | 1-0 |
| Africa de Sud - Premier | 2016/09/21 17:30 | Highlands Park v Kaizer Chiefs | L | 0-1 |
Home History
| Africa de Sud - Premier | 2019/05/11 13:00 | Supersport United v Highlands Park | W | 0-2 |
| Africa de Sud - Premier | 2019/05/04 13:00 | Highlands Park v Bloem Celtic | W | 1-0 |
| Africa de Sud - Premier | 2019/04/27 13:00 | Highlands Park v Polokwane City | L | 0-2 |
| Africa de Sud - Premier | 2019/04/23 17:30 | Cape Town City v Highlands Park | D | 1-1 |
| Africa de Sud - Premier | 2019/04/17 17:30 | Highlands Park v Free State Stars | D | 1-1 |
| Africa de Sud - Premier | 2019/04/13 13:00 | Highlands Park v Maritzburg Utd | W | 1-0 |
| Africa de Sud - Premier | 2019/03/17 13:30 | Chippa United v Highlands Park | D | 1-1 |
| Africa de Sud - Premier | 2019/03/09 13:30 | Highlands Park v Baroka FC | W | 2-1 |
Away History
| Meciuri amicale internationale intercluburi | 2019/07/27 13:15 | Kaizer Chiefs v Orlando Pirates | L | 0-2 |
| Africa de Sud - Cupa | 2019/05/18 17:00 | Kaizer Chiefs v TS Galaxy | L | 0-1 |
| Africa de Sud - Premier | 2019/05/11 13:00 | Chippa United v Kaizer Chiefs | L | 1-0 |
| Africa de Sud - Premier | 2019/05/04 13:00 | Kaizer Chiefs v Free State Stars | D | 1-1 |
| Africa de Sud - Premier | 2019/04/27 18:15 | Bloem Celtic v Kaizer Chiefs | L | 1-0 |
| Africa de Sud - Premier | 2019/04/23 17:30 | Kaizer Chiefs v Golden Arrows | D | 1-1 |
| Africa de Sud - Cupa | 2019/04/20 18:15 | Chippa United v Kaizer Chiefs | W | 2-4 |
| Africa de Sud - Premier | 2019/04/13 13:00 | Black Leopards v Kaizer Chiefs | D | 1-1 |