| South Africa Diski Challenge | 2023/04/30 10:00 | Kaizer Chiefs Reserves v Cape Town City FC Reserves | D | 2-2 |
| 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 | 2023/11/12 08:00 | Royal AM Reserves v Kaizer Chiefs Reserves | D | 2-2 |
| South Africa Diski Challenge | 2023/11/04 08:00 | Kaizer Chiefs Reserves v Richards Bay FC Reserves | D | 0-0 |
| South Africa Diski Challenge | 2023/10/28 08:00 | Golden Arrows Reserves v Kaizer Chiefs Reserves | W | 2-3 |
| South Africa Diski Challenge | 2023/10/21 10:00 | Moroka Swallows Reserves v Kaizer Chiefs Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/10/15 13:00 | Kaizer Chiefs Reserves v Mamelodi Sundowns Reserves | L | 0-1 |
| South Africa Diski Challenge | 2023/09/30 08:00 | Kaizer Chiefs Reserves v Stellenbosch FC Reserves | W | 4-0 |
| South Africa Diski Challenge | 2023/09/24 08:00 | Kaizer Chiefs Reserves v Supersport United Reserves | W | 4-3 |
| South Africa Diski Challenge | 2023/09/17 10:00 | Amazulu Reserves v Kaizer Chiefs Reserves | W | 1-5 |
| South Africa Diski Challenge | 2023/11/12 08:00 | Sekhukhune United Reserves v Cape Town City FC Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/11/05 08:00 | Cape Town City FC Reserves v Amazulu Reserves | W | 1-0 |
| South Africa Diski Challenge | 2023/10/22 08:00 | Cape Town City FC Reserves v Supersport United Reserves | W | 5-2 |
| South Africa Diski Challenge | 2023/09/30 08:00 | Richards Bay FC Reserves v Cape Town City FC Reserves | L | 3-1 |
| South Africa Diski Challenge | 2023/09/17 08:00 | Cape Town City FC Reserves v Stellenbosch FC Reserves | W | 2-0 |
| South Africa Diski Challenge | 2023/09/10 08:00 | Cape Town Spurs Reserves v Cape Town City FC Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/05/13 08:00 | Mamelodi Sundowns Reserves v Cape Town City FC Reserves | L | 4-1 |
| South Africa Diski Challenge | 2023/05/07 08:00 | Cape Town City FC Reserves v TS Galaxy Reserves | L | 1-2 |