| South Africa Diski Challenge | 2023/11/19 10:00 | Kaizer Chiefs Reserves v Cape Town City FC Reserves | D | 1-1 |
| 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 | W | 2-0 |
| 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 | 2021/10/17 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 | L | 2-1 |
| South Africa Diski Challenge | 2019/09/24 13:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | L | 2-4 |
| South Africa Diski Challenge | 2019/02/02 19:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | L | 0-3 |
| 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 | 2024/03/17 08:00 | Amazulu Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2024/05/04 08:00 | Kaizer Chiefs Reserves v Sekhukhune United Reserves | W | 4-1 |
| South Africa Diski Challenge | 2024/04/28 10:00 | Stellenbosch FC Reserves v Kaizer Chiefs Reserves | L | 3-0 |
| South Africa Diski Challenge | 2024/04/21 09:30 | Mamelodi Sundowns Reserves v Kaizer Chiefs Reserves | D | 2-2 |
| South Africa Diski Challenge | 2024/04/07 08:00 | Kaizer Chiefs Reserves v Cape Town Spurs Reserves | L | 1-3 |
| South Africa Diski Challenge | 2024/03/24 13:00 | Orlando Pirates Reserves v Kaizer Chiefs Reserves | W | 0-2 |
| South Africa Diski Challenge | 2024/03/16 08:00 | Kaizer Chiefs Reserves v Golden Arrows Reserves | D | 1-1 |
| South Africa Diski Challenge | 2024/03/03 10:00 | TS Galaxy Reserves v Kaizer Chiefs Reserves | W | 0-1 |
| South Africa Diski Challenge | 2024/02/25 10:00 | Richards Bay FC Reserves v Kaizer Chiefs Reserves | W | 0-5 |