[2] Supersport United 2-0 Highlands Park [6] 2019-12-06 18:00
Stadium: Lucas Moripe Stadium Round: 1
Referee: Khulekani Thusi Home Manager: Kaitano Tembo Away Manager: Owen Da Gama
Head to Head
| South Africa Supa 8 Cup | 2019/10/05 16:00 | Highlands Park v Supersport United | W | 0-1 |
| South Africa Premier | 2019/05/11 13:00 | Supersport United v Highlands Park | L | 0-2 |
| South Africa Premier | 2018/12/23 13:30 | Highlands Park v Supersport United | D | 1-1 |
| South Africa Premier | 2017/02/25 18:15 | Highlands Park v Supersport United | W | 0-1 |
| South Africa Premier | 2016/10/16 13:30 | Supersport United v Highlands Park | W | 4-1 |
Home History
| South Africa Premier | 2019/11/30 18:15 | Supersport United v Stellenbosch FC | D | 1-1 |
| South Africa Premier | 2019/11/27 17:30 | Maritzburg Utd v Supersport United | W | 0-2 |
| South Africa Premier | 2019/11/08 18:00 | Bidvest Wits v Supersport United | W | 0-1 |
| South Africa Premier | 2019/11/05 17:30 | Supersport United v Golden Arrows | D | 0-0 |
| South Africa League Cup | 2019/11/02 18:15 | Supersport United v Golden Arrows | L | 0-1 |
| South Africa Premier | 2019/10/30 17:30 | Bloem Celtic v Supersport United | D | 1-1 |
| South Africa Premier | 2019/10/25 18:00 | Supersport United v Black Leopards | D | 2-2 |
| South Africa League Cup | 2019/10/19 18:15 | Supersport United v Baroka FC | W | 4-3 |
Away History
| South Africa Premier | 2019/11/30 16:00 | Cape Town City v Highlands Park | D | 0-0 |
| South Africa Premier | 2019/11/26 17:30 | Highlands Park v Bidvest Wits | D | 1-1 |
| South Africa Premier | 2019/11/09 13:30 | Stellenbosch FC v Highlands Park | D | 0-0 |
| South Africa Premier | 2019/11/05 17:30 | Bloem Celtic v Highlands Park | L | 3-1 |
| South Africa League Cup | 2019/11/01 18:00 | Maritzburg Utd v Highlands Park | L | 5-4 |
| South Africa Premier | 2019/10/29 17:30 | Highlands Park v Orlando Pirates | L | 0-1 |
| South Africa Premier | 2019/10/26 18:15 | Highlands Park v Chippa United | W | 2-0 |
| South Africa Premier | 2019/10/23 17:30 | Mamelodi Sundowns v Highlands Park | L | 1-0 |