| 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 | 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 | L | 0-1 |
| South Africa Diski Challenge | 2020/02/09 08:00 | Cape Town City FC Reserves v Supersport United Reserves | L | 1-4 |
| South Africa Diski Challenge | 2019/11/24 07:59 | Supersport United Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/03/31 09:27 | Cape Town City FC Reserves v Supersport United Reserves | L | 1-2 |
| South Africa Diski Challenge | 2018/11/25 08:00 | Cape Town City FC Reserves v Supersport United Reserves | W | 2-1 |
| 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 |
| 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 | 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 | 2023/09/24 08:00 | Kaizer Chiefs Reserves v Supersport United Reserves | L | 4-3 |
| South Africa Diski Challenge | 2023/09/09 11:00 | Mamelodi Sundowns Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/05/13 09:30 | Kaizer Chiefs Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/05/06 08:00 | Supersport United Reserves v Moroka Swallows Reserves | W | 3-0 |
| South Africa Diski Challenge | 2023/04/29 08:00 | Golden Arrows Reserves v Supersport United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/04/22 08:00 | Royal AM Reserves v Supersport United Reserves | W | 2-4 |
| 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 | 2023/04/09 08:00 | Supersport United Reserves v Amazulu Reserves | W | 3-0 |