| South Africa Diski Challenge | 2019/08/09 07:53 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2019/12/07 08:00 | Orlando Pirates Reserves v Chippa United Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/11/30 08:01 | Chippa United Reserves v Highlands Park Reserves | L | 1-3 |
| South Africa Diski Challenge | 2019/11/23 07:50 | Chippa United Reserves v Baroka FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/11/17 07:58 | Black Leopards Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2019/11/02 07:59 | Chippa United Reserves v Bloem Celtic Reserves | W | 3-2 |
| South Africa Diski Challenge | 2019/10/20 08:00 | Kaizer Chiefs Reserves v Chippa United Reserves | L | 5-2 |
| 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 | 2019/12/07 07:57 | Stellenbosch FC Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/11/17 07:59 | Stellenbosch FC Reserves v Cape Town City FC Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/11/02 09:59 | Orlando Pirates Reserves v Stellenbosch FC Reserves | L | 2-0 |
| South Africa Diski Challenge | 2019/10/26 08:00 | Stellenbosch FC Reserves v Kaizer Chiefs Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/10/19 08:02 | Stellenbosch FC Reserves v Golden Arrows Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/10/06 10:51 | Stellenbosch FC Reserves v Bloem Celtic Reserves | W | 3-1 |
| South Africa Diski Challenge | 2019/09/24 07:00 | Stellenbosch FC Reserves v Mamelodi Sundowns Reserves | L | 0-3 |
| South Africa Diski Challenge | 2019/09/14 09:59 | Highlands Park Reserves v Stellenbosch FC Reserves | L | 3-1 |