| South Africa Diski Challenge | 2019/02/02 07:57 | Highlands Park Reserves v Chippa United Reserves | W | 4-1 |
| 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 | 2019/01/27 09:59 | Highlands Park Reserves v Orlando Pirates Reserves | D | 0-0 |
| South Africa Diski Challenge | 2019/01/19 08:01 | Highlands Park Reserves v Polokwane City Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/01/12 08:20 | Highlands Park Reserves v Black Leopards Reserves | L | 1-4 |
| 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 |
| South Africa Diski Challenge | 2018/11/18 08:01 | Cape Town City FC Reserves v Chippa United Reserves | L | 3-2 |