| South Africa Diski Challenge | 2019/09/07 10:00 | Highlands Park Reserves v Orlando Pirates Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/08/31 10:01 | Mamelodi Sundowns Reserves v Highlands Park Reserves | L | 1-0 |
| South Africa Diski Challenge | 2019/08/25 08:00 | Highlands Park Reserves v Polokwane City Reserves | W | 3-1 |
| South Africa Diski Challenge | 2019/08/11 10:00 | Highlands Park Reserves v Baroka FC Reserves | L | 0-3 |
| South Africa Diski Shield | 2019/04/13 07:58 | Bidvest Wits Reserves v Highlands Park Reserves | L | 4-2 |
| South Africa Diski Challenge | 2019/04/07 09:58 | Orlando Pirates Reserves v Highlands Park Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/03/31 10:11 | Highlands Park Reserves v Kaizer Chiefs Reserves | L | 1-3 |
| South Africa Diski Challenge | 2019/02/02 07:57 | Highlands Park Reserves v Chippa United Reserves | W | 4-1 |
| South Africa Diski Challenge | 2019/09/08 08:00 | Stellenbosch FC Reserves v Baroka FC Reserves | L | 1-3 |
| South Africa Diski Challenge | 2019/08/09 07:53 | Stellenbosch FC Reserves v Chippa United Reserves | W | 2-1 |