| South Africa Diski Challenge | 2019/10/13 10:00 | Siwelele FC Reserves v Cape Town City FC Reserves | W | 5-0 |
| South Africa Diski Challenge | 2019/10/06 10:51 | Stellenbosch FC Reserves v Siwelele FC Reserves | L | 3-1 |
| 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 10:00 | Siwelele FC Reserves v Kaizer Chiefs Reserves | L | 1-7 |
| South Africa Diski Challenge | 2019/08/25 10:01 | Amazulu Reserves v Siwelele FC Reserves | W | 3-4 |
| South Africa Diski Challenge | 2019/08/09 09:50 | Siwelele FC Reserves v Mamelodi Sundowns Reserves | L | 0-3 |
| South Africa Diski Shield | 2019/04/13 08:00 | Cape Town City FC Reserves v Siwelele FC Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/02/23 11:00 | Kaizer Chiefs Reserves v Siwelele FC Reserves | W | 1-3 |
| 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 |