| South Africa Diski Challenge | 2024/03/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | W | 4-1 |
| 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 | 2024/05/11 08:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | W | 1-0 |
| South Africa Diski Challenge | 2024/05/05 08:00 | Orlando Pirates Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2024/04/28 08:00 | Cape Town City FC Reserves v Cape Town Spurs Reserves | W | 3-1 |
| South Africa Diski Challenge | 2024/04/21 10:00 | Stellenbosch FC Reserves v Cape Town City FC Reserves | L | 4-0 |
| South Africa Diski Challenge | 2024/04/13 08:00 | Golden Arrows Reserves v Cape Town City FC Reserves | W | 1-2 |
| South Africa Diski Challenge | 2024/04/07 08:00 | Cape Town City FC Reserves v Royal AM Reserves | W | 8-0 |
| South Africa Diski Challenge | 2024/03/30 08:00 | Supersport United Reserves v Cape Town City FC Reserves | L | 1-0 |
| South Africa Diski Challenge | 2024/03/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | W | 4-1 |
| 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 |
| 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 |