| South Africa Diski Challenge | 2023/09/09 08:00 | Stellenbosch FC Reserves v Chippa United Reserves | W | 2-0 |
| South Africa Diski Challenge | 2023/04/01 10:00 | Stellenbosch FC Reserves v Chippa United Reserves | W | 2-1 |
| South Africa Diski Shield | 2022/07/16 08:00 | Chippa United Reserves v Stellenbosch FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2019/12/14 07:55 | Chippa United Reserves v Stellenbosch FC Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/08/09 07:53 | Stellenbosch FC Reserves v Chippa United Reserves | W | 2-1 |
| South Africa Diski Challenge | 2024/09/22 10:00 | Stellenbosch FC Reserves v Mamelodi Sundowns Reserves | W | 2-1 |
| South Africa Diski Challenge | 2024/09/15 10:00 | Cape Town City FC Reserves v Stellenbosch FC Reserves | L | 3-1 |
| South Africa Diski Challenge | 2024/09/08 10:00 | Stellenbosch FC Reserves v Richards Bay FC Reserves | W | 2-1 |
| South Africa Diski Challenge | 2024/05/11 09:30 | Stellenbosch FC Reserves v Golden Arrows Reserves | W | 4-3 |
| South Africa Diski Challenge | 2024/05/04 08:00 | Moroka Swallows Reserves v Stellenbosch FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2024/04/28 10:00 | Stellenbosch FC Reserves v Kaizer Chiefs Reserves | W | 3-0 |
| South Africa Diski Challenge | 2024/04/21 10:00 | Stellenbosch FC Reserves v Cape Town City FC Reserves | W | 4-0 |
| South Africa Diski Challenge | 2024/04/14 08:00 | Orlando Pirates Reserves v Stellenbosch FC Reserves | W | 0-1 |
| 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 | 2024/03/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | L | 4-1 |