| 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 | 2019/08/31 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 Challenge | 2019/10/12 08:00 | Polokwane City Reserves v Maritzburg United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/09/22 08:00 | Bidvest Wits Reserves v Maritzburg United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/09/14 08:00 | Maritzburg United Reserves v Cape Town City FC Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/09/07 13:00 | Golden Arrows Reserves v Maritzburg United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/08/10 08:00 | Maritzburg United Reserves v Supersport United Reserves | L | 1-5 |
| South Africa Diski Shield | 2019/04/13 10:03 | Maritzburg United Reserves v Golden Arrows Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/02/03 17:00 | Maritzburg United Reserves v Amazulu Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/01/26 07:59 | Maritzburg United Reserves v Supersport United Reserves | D | 4-4 |