| South Africa Diski Challenge | 2018/11/18 08:01 | Cape Town City FC Reserves v Chippa United Reserves | W | 3-2 |
| South Africa Diski Shield | 2019/04/13 08:00 | Cape Town City FC Reserves v Bloem Celtic Reserves | D | 1-1 |
| South Africa Diski Challenge | 2019/03/31 09:27 | Cape Town City FC Reserves v Supersport United Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/02/23 10:00 | Cape Town City FC Reserves v Polokwane City Reserves | D | 2-2 |
| South Africa Diski Challenge | 2019/02/02 19:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | L | 0-3 |
| South Africa Diski Challenge | 2019/01/26 07:51 | Bloem Celtic Reserves v Cape Town City FC Reserves | L | 1-0 |
| South Africa Diski Challenge | 2019/01/20 08:00 | Cape Town City FC Reserves v Baroka FC Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/01/12 07:51 | Cape Town City FC Reserves v Mamelodi Sundowns Reserves | D | 1-1 |
| South Africa Diski Challenge | 2018/12/02 08:00 | Golden Arrows Reserves v Cape Town City FC Reserves | L | 2-1 |
| 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 | 2019/01/13 10:04 | Chippa United Reserves v Orlando Pirates Reserves | L | 1-2 |
| South Africa Diski Challenge | 2018/12/02 07:59 | Supersport United Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2018/11/25 08:01 | Chippa United Reserves v Mamelodi Sundowns Reserves | W | 5-4 |
| South Africa Diski Challenge | 2018/11/18 08:01 | Cape Town City FC Reserves v Chippa United Reserves | L | 3-2 |