| South Africa Diski Challenge | 2018/12/02 07:59 | Supersport United Reserves v Chippa United Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/09/01 09:58 | Baroka FC Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/08/10 08:00 | Maritzburg United Reserves v Supersport United Reserves | W | 1-5 |
| South Africa Diski Shield | 2019/05/12 08:00 | Supersport United Reserves v Orlando Pirates Reserves | W | 2-0 |
| South Africa Diski Shield | 2019/05/01 10:00 | Supersport United Reserves v Mamelodi Sundowns Reserves | L | 0-1 |
| South Africa Diski Shield | 2019/04/14 08:00 | Supersport United Reserves v Free State Stars Reserves | W | 2-1 |
| 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 | 2019/02/23 10:00 | Free State Stars Reserves v Supersport United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2019/02/02 09:49 | Supersport United Reserves v Bidvest Wits Reserves | W | 4-2 |
| South Africa Diski Challenge | 2019/08/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | W | 0-3 |
| South Africa Diski Challenge | 2019/08/09 07:53 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/02/02 07:57 | Highlands Park Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2019/01/26 07:59 | Amazulu Reserves v Chippa United Reserves | D | 0-0 |
| South Africa Diski Challenge | 2019/01/20 08:00 | Chippa United Reserves v Bidvest Wits Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/01/13 10:04 | Chippa United Reserves v Orlando Pirates Reserves | L | 1-2 |
| South Africa Diski Challenge | 2018/12/02 07:59 | Supersport United Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2018/11/25 08:01 | Chippa United Reserves v Mamelodi Sundowns Reserves | W | 5-4 |