| 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 | 2019/08/09 07:53 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/02/02 07:57 | Highlands Park Reserves v Chippa United Reserves | L | 4-1 |
| South Africa Diski Challenge | 2019/01/26 07:59 | Amazulu Reserves v Chippa United Reserves | D | 0-0 |
| South Africa Diski Challenge | 2019/01/20 08:00 | Chippa United Reserves v Bidvest Wits Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/10/12 08:00 | Bidvest Wits Reserves v Baroka FC Reserves | L | 2-0 |
| South Africa Diski Challenge | 2019/10/05 09:58 | Baroka FC Reserves v Orlando Pirates Reserves | W | 1-0 |
| South Africa Diski Challenge | 2019/09/29 08:00 | Mamelodi Sundowns Reserves v Baroka FC Reserves | L | 5-0 |
| South Africa Diski Challenge | 2019/09/22 07:54 | Baroka FC Reserves v Golden Arrows Reserves | W | 2-0 |
| South Africa Diski Challenge | 2019/09/14 10:00 | Baroka FC Reserves v Siwelele FC Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/09/08 08:00 | Stellenbosch FC Reserves v Baroka FC Reserves | W | 1-3 |
| South Africa Diski Challenge | 2019/09/01 09:58 | Baroka FC Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/08/11 10:00 | Highlands Park Reserves v Baroka FC Reserves | W | 0-3 |