| South Africa Diski Shield | 2019/04/13 07:58 | Bidvest Wits Reserves v Highlands Park Reserves | L | 4-2 |
| South Africa Diski Challenge | 2018/11/17 08:01 | Highlands Park Reserves v Bidvest Wits Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/11/02 08:06 | Supersport United Reserves v Highlands Park Reserves | W | 0-2 |
| South Africa Diski Challenge | 2019/10/27 09:59 | Cape Town City FC Reserves v Highlands Park Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/10/19 09:59 | Highlands Park Reserves v Maritzburg United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/10/12 10:00 | Highlands Park Reserves v Black Leopards Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/10/06 08:00 | Golden Arrows Reserves v Highlands Park Reserves | W | 0-4 |
| South Africa Diski Challenge | 2019/09/28 08:12 | Highlands Park Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/09/14 09:59 | Highlands Park Reserves v Stellenbosch FC Reserves | W | 3-1 |
| South Africa Diski Challenge | 2019/09/07 10:00 | Highlands Park Reserves v Orlando Pirates Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/11/03 10:00 | Cape Town City FC Reserves v Bidvest Wits Reserves | W | 1-2 |
| South Africa Diski Challenge | 2019/10/27 08:00 | Bidvest Wits Reserves v Mamelodi Sundowns Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/10/12 08:00 | Bidvest Wits Reserves v Baroka FC Reserves | W | 2-0 |
| South Africa Diski Challenge | 2019/09/22 08:00 | Bidvest Wits Reserves v Maritzburg United Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/09/15 08:00 | Golden Arrows Reserves v Bidvest Wits Reserves | W | 1-7 |
| South Africa Diski Challenge | 2019/08/31 07:59 | Bidvest Wits Reserves v Kaizer Chiefs Reserves | W | 4-2 |
| South Africa Diski Challenge | 2019/08/24 10:00 | Bidvest Wits Reserves v Orlando Pirates Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/08/11 07:59 | Polokwane City Reserves v Bidvest Wits Reserves | L | 2-1 |