| South Africa Diski Challenge | 2019/09/28 08:12 | Highlands Park Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/02/02 07:57 | Highlands Park Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2019/11/23 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 | 2019/11/02 07:59 | Chippa United Reserves v Bloem Celtic Reserves | W | 3-2 |
| South Africa Diski Challenge | 2019/10/20 08:00 | Kaizer Chiefs Reserves v Chippa United Reserves | L | 5-2 |
| South Africa Diski Challenge | 2019/09/28 08:12 | Highlands Park Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/09/24 10:00 | Chippa United Reserves v Orlando Pirates Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/09/07 08:02 | Supersport United Reserves v Chippa United Reserves | L | 4-0 |
| South Africa Diski Challenge | 2019/08/24 08:00 | Cape Town City FC Reserves v Chippa United Reserves | W | 0-3 |
| South Africa Diski Challenge | 2019/11/23 08:00 | Bloem Celtic Reserves v Highlands Park Reserves | W | 0-2 |
| South Africa Diski Challenge | 2019/11/16 07:59 | Highlands Park Reserves v Bidvest Wits Reserves | L | 1-4 |
| 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 |