Head to Head
| 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 | 2023/09/17 08:00 | Polokwane City Reserves v Chippa United Reserves | W | 0-2 |
| South Africa Diski Challenge | 2023/09/09 08:00 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/04/29 08:00 | TS Galaxy Reserves v Chippa United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/04/16 08:00 | Royal AM Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/04/01 10:00 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/03/12 08:00 | Supersport United Reserves v Chippa United Reserves | L | 5-2 |
| South Africa Diski Challenge | 2023/02/19 08:00 | Moroka Swallows Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2023/01/29 08:00 | Maritzburg United Reserves v Chippa United Reserves | L | 1-0 |
Away History
| South Africa Diski Challenge | 2023/09/23 08:00 | Orlando Pirates Reserves v Moroka Swallows Reserves | W | 4-0 |
| South Africa Diski Challenge | 2023/09/10 13:00 | Kaizer Chiefs Reserves v Orlando Pirates Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/05/13 08:00 | Orlando Pirates Reserves v Golden Arrows Reserves | W | 2-0 |
| South Africa Diski Challenge | 2023/05/06 10:00 | Richards Bay FC Reserves v Orlando Pirates Reserves | D | 0-0 |
| South Africa Diski Challenge | 2023/04/29 10:00 | Orlando Pirates Reserves v Mamelodi Sundowns Reserves | W | 2-1 |
| South Africa Diski Challenge | 2023/04/23 08:00 | Orlando Pirates Reserves v Moroka Swallows Reserves | L | 0-1 |
| South Africa Diski Challenge | 2023/04/15 10:00 | Marumo Gallants Reserves v Orlando Pirates Reserves | D | 0-0 |
| South Africa Diski Challenge | 2023/03/26 09:00 | Orlando Pirates Reserves v Kaizer Chiefs Reserves | W | 3-1 |