[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
| South Africa Premier | 2019/03/02 16:00 | Kaizer Chiefs v Highlands Park | L | 3-2 |
| South Africa Premier | 2018/10/02 17:30 | Highlands Park v Kaizer Chiefs | D | 0-0 |
| South Africa Premier | 2017/02/18 16:00 | Kaizer Chiefs v Highlands Park | L | 1-0 |
| South Africa Premier | 2016/09/21 17:30 | Highlands Park v Kaizer Chiefs | L | 0-1 |