[7] Montenegro 1-0 Free State Stars [14] 2019-01-11 15:30
Stadium: Lucas Moripe Stadium Round: 1
Referee: Eugene Mdluli Home Manager: Kaitano Tembo Away Manager: Nikola Kavazovic
Head to Head
| South Africa Premier | 2018/11/10 18:15 | Free State Stars v Supersport United | W | 0-1 |
| South Africa Premier | 2018/04/25 17:30 | Supersport United v Free State Stars | W | 3-2 |
| South Africa Premier | 2017/12/13 17:30 | Free State Stars v Supersport United | L | 1-0 |
| South Africa Premier | 2017/02/15 17:30 | Free State Stars v Supersport United | D | 0-0 |
| South Africa Premier | 2016/09/24 18:15 | Supersport United v Free State Stars | D | 0-0 |
| South Africa Premier | 2016/01/30 16:00 | Supersport United v Free State Stars | W | 1-0 |
| South Africa Premier | 2015/11/01 13:30 | Free State Stars v Supersport United | D | 0-0 |
| South Africa Premier | 2015/02/11 17:30 | Supersport United v Free State Stars | D | 2-2 |
Home History
| South Africa Premier | 2019/01/05 18:15 | Supersport United v Cape Town City | L | 0-1 |
| South Africa Premier | 2018/12/23 13:30 | Highlands Park v Supersport United | D | 1-1 |
| South Africa Premier | 2018/12/15 16:00 | Supersport United v Maritzburg Utd | W | 1-0 |
| South Africa Premier | 2018/12/12 17:30 | Kaizer Chiefs v Supersport United | L | 1-0 |
| South Africa Premier | 2018/12/02 13:30 | Supersport United v Mamelodi Sundowns | L | 1-2 |
| South Africa Premier | 2018/11/28 17:30 | Bloem Celtic v Supersport United | D | 0-0 |
| South Africa Premier | 2018/11/10 18:15 | Free State Stars v Supersport United | W | 0-1 |
| South Africa League Cup | 2018/11/04 13:00 | Kaizer Chiefs v Supersport United | L | 1-0 |
Away History
| South Africa Premier | 2019/01/09 17:30 | Maritzburg Utd v Free State Stars | W | 1-2 |
| South Africa Premier | 2019/01/05 16:00 | Free State Stars v Bidvest Wits | L | 1-2 |
| South Africa Premier | 2018/12/11 17:30 | Free State Stars v Orlando Pirates | L | 1-3 |
| CAF Confederations Cup | 2018/12/05 13:30 | Mukura v Free State Stars | L | 1-0 |
| CAF Confederations Cup | 2018/11/28 13:00 | Free State Stars v Mukura | D | 0-0 |
| South Africa Premier | 2018/11/10 18:15 | Free State Stars v Supersport United | L | 0-1 |
| South Africa Premier | 2018/11/07 17:30 | Mamelodi Sundowns v Free State Stars | L | 3-1 |
| South Africa Premier | 2018/10/28 13:30 | Black Leopards v Free State Stars | D | 1-1 |