| South Africa Diski Challenge | 2022/10/30 08:00 | Cape Town City FC Reserves v Supersport United Reserves | D | 0-0 |
| South Africa Diski Challenge | 2022/02/06 08:00 | Cape Town City FC Reserves v Supersport United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2020/02/09 08:00 | Cape Town City FC Reserves v Supersport United Reserves | W | 1-4 |
| South Africa Diski Challenge | 2019/11/24 07:59 | Supersport United Reserves v Cape Town City FC Reserves | W | 3-2 |
| South Africa Diski Challenge | 2019/03/31 09:27 | Cape Town City FC Reserves v Supersport United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2018/11/25 08:00 | Cape Town City FC Reserves v Supersport United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/04/09 08:00 | Supersport United Reserves v Amazulu Reserves | W | 3-0 |
| South Africa Diski Challenge | 2023/04/02 08:00 | Sekhukhune United Reserves v Supersport United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2023/03/25 08:00 | Mamelodi Sundowns Reserves v Supersport United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/03/19 08:00 | Supersport United Reserves v Maritzburg United Reserves | W | 2-1 |
| South Africa Diski Challenge | 2023/03/12 08:00 | Supersport United Reserves v Chippa United Reserves | W | 5-2 |
| South Africa Diski Challenge | 2023/03/04 08:00 | Orlando Pirates Reserves v Supersport United Reserves | W | 0-2 |
| South Africa Diski Challenge | 2023/02/18 08:00 | TS Galaxy Reserves v Supersport United Reserves | W | 0-4 |
| South Africa Diski Challenge | 2023/02/11 09:00 | Supersport United Reserves v Richards Bay FC Reserves | W | 3-0 |
| 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 |
| South Africa Diski Challenge | 2023/02/19 08:00 | Cape Town City FC Reserves v Marumo Gallants Reserves | D | 0-0 |
| South Africa Diski Challenge | 2023/02/11 09:00 | Golden Arrows Reserves v Cape Town City FC Reserves | L | 3-2 |