Head to Head
| South Africa Diski Challenge | 2023/10/14 11:00 | Chippa United Reserves v Orlando Pirates Reserves | L | 0-3 |
| South Africa Diski Challenge | 2023/01/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | L | 3-1 |
| South Africa Diski Challenge | 2019/12/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/09/24 10:00 | Chippa United Reserves v Orlando Pirates Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/01/13 10:04 | Chippa United Reserves v Orlando Pirates Reserves | L | 1-2 |
Home History
| South Africa Diski Challenge | 2024/04/14 08:00 | Cape Town Spurs Reserves v Chippa United Reserves | L | 4-0 |
| South Africa Diski Challenge | 2024/04/07 08:00 | Mamelodi Sundowns Reserves v Chippa United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2024/03/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2024/03/09 08:00 | Royal AM Reserves v Chippa United Reserves | L | 5-2 |
| South Africa Diski Challenge | 2024/02/24 08:00 | Supersport United Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2024/02/17 08:00 | Chippa United Reserves v Amazulu Reserves | L | 0-3 |
| South Africa Diski Challenge | 2024/02/10 08:00 | Richards Bay FC Reserves v Chippa United Reserves | W | 1-3 |
| South Africa Diski Challenge | 2024/01/27 09:00 | Amazulu Reserves v Chippa United Reserves | W | 1-3 |
Away History
| South Africa Diski Challenge | 2024/04/14 08:00 | Orlando Pirates Reserves v Stellenbosch FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2024/04/06 10:00 | Moroka Swallows Reserves v Orlando Pirates Reserves | W | 0-4 |
| South Africa Diski Challenge | 2024/03/30 10:00 | Sekhukhune United Reserves v Orlando Pirates Reserves | D | 0-0 |
| South Africa Diski Challenge | 2024/03/24 13:00 | Orlando Pirates Reserves v Kaizer Chiefs Reserves | L | 0-2 |
| South Africa Diski Challenge | 2024/03/10 08:00 | Cape Town Spurs Reserves v Orlando Pirates Reserves | L | 2-1 |
| South Africa Diski Challenge | 2024/02/24 10:00 | Royal AM Reserves v Orlando Pirates Reserves | W | 3-5 |
| South Africa Diski Challenge | 2024/02/11 12:00 | Mamelodi Sundowns Reserves v Orlando Pirates Reserves | L | 1-0 |
| South Africa Diski Challenge | 2024/01/27 11:00 | Stellenbosch FC Reserves v Orlando Pirates Reserves | L | 1-0 |