| 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 | 2023/03/04 08:00 | Orlando Pirates Reserves v Supersport United Reserves | W | 0-2 |
| South Africa Diski Challenge | 2023/02/18 08:00 | TS Galaxy Reserves v Supersport United Reserves | W | 0-4 |
| South Africa Diski Challenge | 2023/02/11 09:00 | Supersport United Reserves v Richards Bay FC Reserves | W | 3-0 |
| South Africa Diski Challenge | 2023/01/22 10:30 | Supersport United Reserves v Kaizer Chiefs Reserves | W | 2-0 |
| South Africa Diski Challenge | 2023/01/15 09:00 | Supersport United Reserves v Royal AM Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/01/08 08:00 | Amazulu Reserves v Supersport United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2022/11/19 10:00 | Supersport United Reserves v Golden Arrows Reserves | L | 1-3 |
| South Africa Diski Challenge | 2022/11/13 08:00 | Supersport United Reserves v Sekhukhune United Reserves | W | 6-1 |
| 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 |
| South Africa Diski Challenge | 2023/01/22 10:00 | Richards Bay FC Reserves v Chippa United Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/01/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | L | 3-1 |
| 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 |