| South Africa Diski Challenge | 2023/10/29 08:00 | Sekhukhune United Reserves v Chippa United Reserves | L | 4-2 |
| South Africa Diski Challenge | 2024/09/29 08:00 | Stellenbosch FC Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2024/09/21 08:00 | Amazulu Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2024/09/15 08:00 | Supersport United Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2024/09/08 11:00 | Kaizer Chiefs Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2024/05/04 07:30 | Golden Arrows Reserves v Chippa United Reserves | D | 3-3 |
| South Africa Diski Challenge | 2024/04/21 07:30 | Chippa United Reserves v Orlando Pirates Reserves | L | 0-1 |
| 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 | 2024/09/21 08:00 | Orlando Pirates Reserves v Sekhukhune United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2024/09/14 08:00 | Kaizer Chiefs Reserves v Sekhukhune United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2024/09/08 08:00 | Sekhukhune United Reserves v Golden Arrows Reserves | W | 3-0 |
| South Africa Diski Challenge | 2024/09/01 08:00 | Cape Town City FC Reserves v Sekhukhune United Reserves | L | 6-2 |
| South Africa Diski Challenge | 2024/05/11 08:00 | Sekhukhune United Reserves v Royal AM Reserves | D | 3-3 |
| South Africa Diski Challenge | 2024/05/04 08:00 | Kaizer Chiefs Reserves v Sekhukhune United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2024/04/27 10:00 | Sekhukhune United Reserves v Supersport United Reserves | W | 5-0 |
| South Africa Diski Challenge | 2024/04/14 10:12 | Sekhukhune United Reserves v Mamelodi Sundowns Reserves | W | 1-0 |