| 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 | 2022/04/03 08:00 | Cape Town City FC Reserves v Golden Arrows Reserves | D | 0-0 |
| South Africa Diski Challenge | 2022/03/20 08:00 | Cape Town City FC Reserves v Mamelodi Sundowns Reserves | L | 1-3 |
| South Africa Diski Challenge | 2022/03/06 08:00 | Cape Town City FC Reserves v Royal AM Reserves | W | 5-1 |
| South Africa Diski Challenge | 2022/02/20 08:00 | Cape Town City FC Reserves v Baroka FC Reserves | W | 4-3 |
| South Africa Diski Challenge | 2022/02/06 08:00 | Cape Town City FC Reserves v Supersport United Reserves | L | 0-1 |
| South Africa Diski Challenge | 2022/01/23 08:00 | Cape Town City FC Reserves v Moroka Swallows Reserves | L | 1-2 |
| South Africa Diski Challenge | 2021/11/14 08:00 | Kaizer Chiefs Reserves v Cape Town City FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2021/11/07 08:00 | Cape Town City FC Reserves v Sekhukhune United Reserves | W | 3-1 |
| South Africa Diski Challenge | 2022/04/16 08:00 | Maritzburg United Reserves v Chippa United Reserves | W | 3-6 |
| South Africa Diski Challenge | 2022/01/23 10:30 | Chippa United Reserves v Kaizer Chiefs Reserves | L | 1-4 |
| South Africa Diski Challenge | 2021/10/10 08:00 | Baroka FC Reserves v Chippa United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2020/12/05 09:00 | Chippa United Reserves v Black Leopards Reserves | W | 3-1 |
| South Africa Diski Challenge | 2020/03/14 08:00 | Baroka FC Reserves v Chippa United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2020/02/29 07:59 | Bloem Celtic Reserves v Chippa United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2020/02/22 07:54 | Chippa United Reserves v Supersport United Reserves | W | 4-2 |
| South Africa Diski Challenge | 2020/02/15 07:59 | Maritzburg United Reserves v Chippa United Reserves | D | 2-2 |