| South Africa Diski Challenge | 2022/09/18 08:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | L | 2-0 |
| South Africa Diski Challenge | 2021/11/14 08:00 | Kaizer Chiefs Reserves v Cape Town City FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2021/10/17 08:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | D | 2-2 |
| South Africa Diski Challenge | 2020/02/23 07:52 | Kaizer Chiefs Reserves v Cape Town City FC Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/09/24 13:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | W | 2-4 |
| South Africa Diski Challenge | 2019/02/02 19:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | W | 0-3 |
| South Africa Diski Challenge | 2023/04/23 10:00 | Stellenbosch FC Reserves v Kaizer Chiefs Reserves | L | 5-2 |
| South Africa Diski Challenge | 2023/04/19 08:00 | Kaizer Chiefs Reserves v Maritzburg United Reserves | W | 5-0 |
| South Africa Diski Challenge | 2023/04/16 08:00 | TS Galaxy Reserves v Kaizer Chiefs Reserves | L | 6-3 |
| South Africa Diski Challenge | 2023/04/08 08:00 | Kaizer Chiefs Reserves v Marumo Gallants Reserves | W | 3-0 |
| South Africa Diski Challenge | 2023/04/02 10:00 | Royal AM Reserves v Kaizer Chiefs Reserves | D | 0-0 |
| South Africa Diski Challenge | 2023/03/26 09:00 | Orlando Pirates Reserves v Kaizer Chiefs Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/03/18 08:00 | Kaizer Chiefs Reserves v Moroka Swallows Reserves | W | 3-1 |
| South Africa Diski Challenge | 2023/02/19 10:00 | Kaizer Chiefs Reserves v Mamelodi Sundowns Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/04/23 08:00 | Cape Town City FC Reserves v Maritzburg United Reserves | L | 0-1 |
| South Africa Diski Challenge | 2023/04/16 10:00 | Supersport United Reserves v Cape Town City FC Reserves | D | 3-3 |
| South Africa Diski Challenge | 2023/04/02 08:00 | Cape Town City FC Reserves v Moroka Swallows Reserves | W | 5-1 |
| South Africa Diski Challenge | 2023/03/26 07:00 | Cape Town City FC Reserves v Stellenbosch FC Reserves | W | 3-2 |
| South Africa Diski Challenge | 2023/03/19 08:00 | Richards Bay FC Reserves v Cape Town City FC Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/03/12 08:00 | Cape Town City FC Reserves v Orlando Pirates Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/03/05 08:00 | Cape Town City FC Reserves v Royal AM Reserves | W | 1-0 |
| South Africa Diski Challenge | 2023/02/26 08:00 | Amazulu Reserves v Cape Town City FC Reserves | W | 0-1 |