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