| South Africa Diski Challenge | 2019/03/31 10:11 | Highlands Park Reserves v Kaizer Chiefs Reserves | L | 1-3 |
| South Africa Diski Challenge | 2018/09/24 11:00 | Highlands Park Reserves v Kaizer Chiefs Reserves | D | 0-0 |
| South Africa Diski Challenge | 2019/12/14 09:58 | Highlands Park Reserves v Cape Town City FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/12/07 07:58 | Maritzburg United Reserves v Highlands Park Reserves | W | 0-2 |
| South Africa Diski Challenge | 2019/11/30 08:01 | Chippa United Reserves v Highlands Park Reserves | W | 1-3 |
| 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 | 2019/12/16 13:00 | Polokwane City Reserves v Kaizer Chiefs Reserves | L | 2-0 |
| South Africa Diski Challenge | 2019/12/08 10:01 | Kaizer Chiefs Reserves v Golden Arrows Reserves | W | 5-1 |
| South Africa Diski Challenge | 2019/11/30 11:00 | Kaizer Chiefs Reserves v Maritzburg United Reserves | W | 3-0 |
| South Africa Diski Challenge | 2019/11/24 11:00 | Amazulu Reserves v Kaizer Chiefs Reserves | D | 2-2 |
| South Africa Diski Challenge | 2019/11/16 13:00 | Kaizer Chiefs Reserves v Orlando Pirates Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/10/26 08:00 | Stellenbosch FC Reserves v Kaizer Chiefs Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/10/20 08:00 | Kaizer Chiefs Reserves v Chippa United Reserves | W | 5-2 |
| South Africa Diski Challenge | 2019/09/29 08:00 | Kaizer Chiefs Reserves v Black Leopards Reserves | D | 0-0 |