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