| South Africa Diski Challenge | 2023/03/12 08:00 | Supersport United Reserves v Chippa United Reserves | W | 5-2 |
| South Africa Diski Challenge | 2020/02/22 07:54 | Chippa United Reserves v Supersport United Reserves | L | 4-2 |
| South Africa Diski Challenge | 2019/09/07 08:02 | Supersport United Reserves v Chippa United Reserves | W | 4-0 |
| South Africa Diski Challenge | 2018/12/02 07:59 | Supersport United Reserves v Chippa United Reserves | W | 1-0 |
| South Africa Diski Challenge | 2024/02/18 10:00 | Stellenbosch FC Reserves v Supersport United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2024/02/10 12:00 | Supersport United Reserves v Kaizer Chiefs Reserves | W | 1-0 |
| 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 | 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 |
| South Africa Diski Challenge | 2024/01/13 11:00 | Kaizer Chiefs Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/11/11 08:00 | Moroka Swallows Reserves v Chippa United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2023/10/29 08:00 | Sekhukhune United Reserves v Chippa United Reserves | L | 4-2 |
| South Africa Diski Challenge | 2023/10/14 11:00 | Chippa United Reserves v Orlando Pirates Reserves | L | 0-3 |
| South Africa Diski Challenge | 2023/09/17 08:00 | Polokwane City Reserves v Chippa United Reserves | W | 0-2 |