| South Africa Diski Challenge | 2023/10/21 08:00 | Orlando Pirates Reserves v Sekhukhune United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/10/14 13:00 | TS Galaxy Reserves v Sekhukhune United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/10/07 07:00 | Sekhukhune United Reserves v Richards Bay FC Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/10/01 08:00 | Royal AM Reserves v Sekhukhune United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/09/10 11:00 | Sekhukhune United Reserves v Polokwane City Reserves | W | 2-0 |
| South Africa Diski Challenge | 2023/05/13 08:00 | Stellenbosch FC Reserves v Sekhukhune United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2023/04/30 08:00 | Moroka Swallows Reserves v Sekhukhune United Reserves | W | 2-4 |
| South Africa Diski Challenge | 2023/04/16 10:00 | Amazulu Reserves v Sekhukhune United Reserves | D | 1-1 |
| 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 |
| 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 |