| 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 |
| South Africa Reserve League | 2018/10/27 08:04 | Kaizer Chiefs Reserves v Chippa United Reserves | L | 10-0 |