| 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 | 2018/09/08 10:00 | Highlands Park Reserves v Cape Town City FC Reserves | L | 0-3 |
| 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 | 2019/10/12 10:00 | Highlands Park Reserves v Black Leopards Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/12/08 08:00 | Cape Town City FC Reserves v Polokwane City Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/12/01 08:00 | Cape Town City FC Reserves v Baroka FC Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/11/24 07:59 | Supersport United Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/11/17 07:59 | Stellenbosch FC Reserves v Cape Town City FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2019/11/03 10:00 | Cape Town City FC Reserves v Bidvest Wits Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/10/27 09:59 | Cape Town City FC Reserves v Highlands Park Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/10/13 10:00 | Bloem Celtic Reserves v Cape Town City FC Reserves | L | 5-0 |
| South Africa Diski Challenge | 2019/09/28 07:58 | Orlando Pirates Reserves v Cape Town City FC Reserves | W | 2-3 |