| 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 | 2023/03/26 07:00 | Cape Town City FC Reserves v Stellenbosch FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2023/03/19 10:00 | Stellenbosch FC Reserves v Orlando Pirates Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/03/11 08:00 | Maritzburg United Reserves v Stellenbosch FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2023/02/25 08:00 | Golden Arrows Reserves v Stellenbosch FC Reserves | W | 1-3 |
| South Africa Diski Challenge | 2023/02/22 08:00 | Richards Bay FC Reserves v Stellenbosch FC Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/02/12 11:00 | Stellenbosch FC Reserves v Moroka Swallows Reserves | W | 1-0 |
| South Africa Diski Challenge | 2023/01/29 08:00 | Sekhukhune United Reserves v Stellenbosch FC Reserves | D | 3-3 |
| South Africa Diski Challenge | 2023/01/22 08:00 | Moroka Swallows Reserves v Stellenbosch FC 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 |
| 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 |