| South Africa Diski Challenge | 2022/10/09 08:00 | Cape Town City FC Reserves v Chippa United Reserves | W | 3-1 |
| South Africa Diski Challenge | 2022/04/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | L | 1-3 |
| South Africa Diski Challenge | 2019/08/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | L | 0-3 |
| South Africa Diski Challenge | 2018/11/18 08:01 | Cape Town City FC Reserves v Chippa United Reserves | W | 3-2 |
| South Africa Diski Challenge | 2024/03/17 08:00 | Amazulu Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2024/03/10 08:00 | Cape Town City FC Reserves v Polokwane City Reserves | W | 6-1 |
| South Africa Diski Challenge | 2024/03/02 08:00 | Mamelodi Sundowns Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2024/02/25 08:00 | Cape Town City FC Reserves v Sekhukhune United Reserves | W | 3-1 |
| South Africa Diski Challenge | 2024/02/18 08:00 | Cape Town City FC Reserves v Richards Bay FC Reserves | W | 2-1 |
| South Africa Diski Challenge | 2024/02/10 08:00 | Moroka Swallows Reserves v Cape Town City FC Reserves | D | 0-0 |
| South Africa Diski Challenge | 2024/02/04 08:00 | Cape Town City FC Reserves v TS Galaxy Reserves | W | 3-0 |
| South Africa Diski Challenge | 2024/01/28 09:00 | Cape Town City FC Reserves v Mamelodi Sundowns Reserves | L | 0-2 |
| South Africa Diski Challenge | 2024/03/09 08:00 | Royal AM Reserves v Chippa United Reserves | L | 5-2 |
| South Africa Diski Challenge | 2024/02/24 08:00 | Supersport United Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2024/02/17 08:00 | Chippa United Reserves v Amazulu Reserves | L | 0-3 |
| South Africa Diski Challenge | 2024/02/10 08:00 | Richards Bay FC Reserves v Chippa United Reserves | W | 1-3 |
| South Africa Diski Challenge | 2024/01/27 09:00 | Amazulu Reserves v Chippa United Reserves | W | 1-3 |
| South Africa Diski Challenge | 2024/01/13 11:00 | Kaizer Chiefs Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/11/11 08:00 | Moroka Swallows Reserves v Chippa United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2023/10/29 08:00 | Sekhukhune United Reserves v Chippa United Reserves | L | 4-2 |