| South Africa Diski Challenge | 2019/11/17 07:58 | Black Leopards Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2020/03/14 08:00 | Baroka FC Reserves v Chippa United Reserves | W | 1-2 |
| South Africa Diski Challenge | 2020/02/29 07:59 | Bloem Celtic Reserves v Chippa United Reserves | W | 0-1 |
| South Africa Diski Challenge | 2020/02/22 07:54 | Chippa United Reserves v Supersport United Reserves | W | 4-2 |
| South Africa Diski Challenge | 2020/02/15 07:59 | Maritzburg United Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2020/02/09 07:00 | Amazulu Reserves v Chippa United Reserves | L | 2-1 |
| 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 | 2020/03/15 08:00 | Black Leopards Reserves v Polokwane City Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/03/08 07:51 | Bidvest Wits Reserves v Black Leopards Reserves | L | 3-2 |
| South Africa Diski Challenge | 2020/03/01 08:00 | Cape Town City FC Reserves v Black Leopards Reserves | D | 3-3 |
| South Africa Diski Challenge | 2020/02/22 10:00 | Stellenbosch FC Reserves v Black Leopards Reserves | L | 3-1 |
| South Africa Diski Challenge | 2020/02/09 07:04 | Black Leopards Reserves v Maritzburg United Reserves | L | 1-2 |
| South Africa Diski Challenge | 2020/02/02 07:52 | Mamelodi Sundowns Reserves v Black Leopards Reserves | L | 4-1 |
| South Africa Diski Challenge | 2020/01/19 09:55 | Amazulu Reserves v Black Leopards Reserves | L | 3-1 |
| South Africa Diski Challenge | 2020/01/11 08:00 | Black Leopards Reserves v Supersport United Reserves | L | 0-1 |