| South Africa Diski Challenge | 2019/09/07 08:02 | Supersport United Reserves v Chippa United Reserves | L | 4-0 |
| South Africa Diski Challenge | 2018/12/02 07:59 | Supersport United Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2020/01/25 08:00 | Polokwane City Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/01/18 08:00 | Chippa United Reserves v Mamelodi Sundowns Reserves | W | 3-1 |
| South Africa Diski Challenge | 2020/01/12 08:00 | Golden Arrows Reserves v Chippa United Reserves | D | 4-4 |
| South Africa Diski Challenge | 2019/12/14 07:55 | Chippa United Reserves v Stellenbosch FC Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/12/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/11/30 08:01 | Chippa United Reserves v Highlands Park Reserves | L | 1-3 |
| South Africa Diski Challenge | 2019/11/23 07:50 | Chippa United Reserves v Baroka FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/11/17 07:58 | Black Leopards Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2020/01/25 10:00 | Supersport United Reserves v Orlando Pirates Reserves | L | 0-3 |
| South Africa Diski Challenge | 2020/01/19 09:55 | Kaizer Chiefs Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/01/11 08:00 | Black Leopards Reserves v Supersport United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2019/12/14 11:00 | Bidvest Wits Reserves v Supersport United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/12/14 07:58 | Bidvest Wits Reserves v Supersport United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/12/07 07:57 | Stellenbosch FC Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/12/01 07:58 | Supersport United Reserves v Siwelele FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/11/24 07:59 | Supersport United Reserves v Cape Town City FC Reserves | W | 3-2 |