Head to Head
| Südafrika - Diski Challenge | 2019/09/07 10:00 | Highlands Park - Reserve v Orlando Pirates - Reserve | L | 1-0 |
| Südafrika - Diski Challenge | 2019/04/07 09:58 | Orlando Pirates - Reserve v Highlands Park - Reserve | W | 2-1 |
| Südafrika - Diski Challenge | 2019/01/27 09:59 | Highlands Park - Reserve v Orlando Pirates - Reserve | D | 0-0 |
Home History
| Südafrika - Diski Challenge | 2020/02/29 09:57 | Orlando Pirates - Reserve v Maritzburg United - Reserve | W | 3-0 |
| Südafrika - Diski Challenge | 2020/02/23 08:00 | Orlando Pirates - Reserve v Golden Arrows - Reserve | W | 3-0 |
| Südafrika - Diski Challenge | 2020/02/16 11:00 | Orlando Pirates - Reserve v Kaizer Chiefs - Reserve | W | 2-0 |
| Südafrika - Diski Challenge | 2020/02/01 07:58 | Stellenbosch FC - Reserve v Orlando Pirates - Reserve | L | 2-1 |
| Südafrika - Diski Challenge | 2020/01/25 10:00 | Supersport United - Reserve v Orlando Pirates - Reserve | W | 0-3 |
| Südafrika - Diski Challenge | 2020/01/19 08:04 | Cape Town City FC - Reserve v Orlando Pirates - Reserve | W | 0-1 |
| Südafrika - Diski Challenge | 2020/01/11 10:00 | Orlando Pirates - Reserve v Mamelodi Sundowns - Reserve | W | 1-0 |
| Südafrika - Diski Challenge | 2019/12/15 14:00 | Black Leopards - Reserve v Orlando Pirates - Reserve | W | 0-4 |
Away History
| Südafrika - Diski Challenge | 2020/02/16 09:00 | Bidvest Wits - Reserve v Highlands Park - Reserve | L | 1-0 |
| Südafrika - Diski Challenge | 2020/02/09 09:59 | Highlands Park - Reserve v Mamelodi Sundowns - Reserve | D | 1-1 |
| Südafrika - Diski Challenge | 2020/02/01 07:59 | Polokwane City - Reserve v Highlands Park - Reserve | W | 0-1 |
| Südafrika - Diski Challenge | 2020/01/18 10:00 | Highlands Park - Reserve v Bloem Celtic - Reserve | W | 1-0 |
| Südafrika - Diski Challenge | 2020/01/12 10:04 | Highlands Park - Reserve v Kaizer Chiefs - Reserve | L | 1-4 |
| Südafrika - Diski Challenge | 2019/12/14 09:58 | Highlands Park - Reserve v Cape Town City FC - Reserve | L | 0-1 |
| Südafrika - Diski Challenge | 2019/12/07 07:58 | Maritzburg United - Reserve v Highlands Park - Reserve | W | 0-2 |
| Südafrika - Diski Challenge | 2019/11/30 08:01 | Chippa United - Reserve v Highlands Park - Reserve | W | 1-3 |