Head to Head
| South Africa Diski Challenge | 2019/12/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | W | 3-2 |
| South Africa Diski Challenge | 2019/09/24 10:00 | Chippa United Reserves v Orlando Pirates Reserves | W | 0-2 |
| South Africa Diski Challenge | 2019/01/13 10:04 | Chippa United Reserves v Orlando Pirates Reserves | W | 1-2 |
Home History
| South Africa Diski Challenge | 2022/11/19 10:00 | Sekhukhune United Reserves v Orlando Pirates Reserves | W | 0-2 |
| South Africa Diski Challenge | 2022/11/12 09:00 | Golden Arrows Reserves v Orlando Pirates Reserves | W | 0-2 |
| South Africa Diski Challenge | 2022/11/05 10:30 | Orlando Pirates Reserves v Marumo Gallants Reserves | W | 4-1 |
| South Africa Diski Challenge | 2022/10/29 10:00 | Orlando Pirates Reserves v Maritzburg United Reserves | W | 1-0 |
| South Africa Diski Challenge | 2022/10/22 08:00 | Supersport United Reserves v Orlando Pirates Reserves | D | 1-1 |
| South Africa Diski Challenge | 2022/10/15 08:00 | Royal AM Reserves v Orlando Pirates Reserves | D | 2-2 |
| South Africa Diski Challenge | 2022/10/08 10:00 | Orlando Pirates Reserves v Amazulu Reserves | L | 0-1 |
| South Africa Diski Challenge | 2022/10/02 10:30 | Moroka Swallows Reserves v Orlando Pirates Reserves | W | 0-2 |
Away History
| South Africa Diski Challenge | 2022/11/19 08:00 | Chippa United Reserves v Moroka Swallows Reserves | W | 3-0 |
| South Africa Diski Challenge | 2022/10/22 08:00 | Golden Arrows Reserves v Chippa United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2022/10/15 08:00 | Chippa United Reserves v Mamelodi Sundowns Reserves | L | 0-1 |
| South Africa Diski Challenge | 2022/10/09 08:00 | Cape Town City FC Reserves v Chippa United Reserves | L | 3-1 |
| South Africa Diski Challenge | 2022/09/25 12:00 | Kaizer Chiefs Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2022/09/18 10:00 | Amazulu Reserves v Chippa United Reserves | W | 0-1 |
| South Africa Diski Shield | 2022/07/16 08:00 | Chippa United Reserves v Stellenbosch FC Reserves | L | 0-1 |
| South Africa Diski Shield | 2022/07/09 08:00 | TS Galaxy Reserves v Chippa United Reserves | W | 0-1 |