Head to Head
| South Africa Diski Challenge | 2023/11/18 10:00 | Supersport United Reserves v Orlando Pirates Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/03/04 08:00 | Orlando Pirates Reserves v Supersport United Reserves | L | 0-2 |
| South Africa Diski Challenge | 2022/10/22 08:00 | Supersport United Reserves v Orlando Pirates Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/12/05 11:00 | Supersport United Reserves v Orlando Pirates Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/01/25 10:00 | Supersport United Reserves v Orlando Pirates Reserves | W | 0-3 |
| South Africa Diski Shield | 2019/05/12 08:00 | Supersport United Reserves v Orlando Pirates Reserves | L | 2-0 |
| South Africa Diski Challenge | 2019/01/19 09:59 | Orlando Pirates Reserves v Supersport United Reserves | L | 0-1 |
Home History
| South Africa Diski Challenge | 2024/01/27 11:00 | Stellenbosch FC Reserves v Orlando Pirates Reserves | L | 1-0 |
| South Africa Diski Challenge | 2024/01/20 13:00 | Golden Arrows Reserves v Orlando Pirates Reserves | W | 0-3 |
| South Africa Diski Challenge | 2024/01/14 13:00 | Orlando Pirates Reserves v Mamelodi Sundowns Reserves | W | 4-1 |
| South Africa Diski Challenge | 2023/11/25 08:00 | Orlando Pirates Reserves v Cape Town Spurs Reserves | W | 3-1 |
| South Africa Diski Challenge | 2023/11/18 10:00 | Supersport United Reserves v Orlando Pirates Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/11/11 10:00 | TS Galaxy Reserves v Orlando Pirates Reserves | W | 0-2 |
| South Africa Diski Challenge | 2023/10/29 10:00 | Amazulu Reserves v Orlando Pirates Reserves | W | 0-3 |
| South Africa Diski Challenge | 2023/10/21 08:00 | Orlando Pirates Reserves v Sekhukhune United Reserves | D | 1-1 |
Away History
| South Africa Diski Challenge | 2024/01/28 08:00 | Supersport United Reserves v Polokwane City Reserves | D | 0-0 |
| South Africa Diski Challenge | 2024/01/20 10:00 | Moroka Swallows Reserves v Supersport United Reserves | W | 0-5 |
| South Africa Diski Challenge | 2024/01/13 13:00 | Supersport United Reserves v Stellenbosch FC Reserves | L | 1-2 |
| South Africa Diski Challenge | 2023/11/26 08:00 | Royal AM Reserves v Supersport United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/11/18 10:00 | Supersport United Reserves v Orlando Pirates Reserves | W | 3-1 |
| South Africa Diski Challenge | 2023/11/12 08:00 | Cape Town Spurs Reserves v Supersport United Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/11/05 10:00 | Supersport United Reserves v TS Galaxy Reserves | W | 3-1 |
| South Africa Diski Challenge | 2023/10/28 10:00 | Richards Bay FC Reserves v Supersport United Reserves | W | 0-2 |