| South Africa Diski Challenge | 2019/09/24 13:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | W | 2-4 |
| South Africa Diski Challenge | 2019/02/02 19:00 | Cape Town City FC Reserves v Kaizer Chiefs Reserves | W | 0-3 |
| South Africa Diski Challenge | 2020/02/16 11:00 | Orlando Pirates Reserves v Kaizer Chiefs Reserves | L | 2-0 |
| South Africa Diski Challenge | 2020/02/08 07:59 | Baroka FC Reserves v Kaizer Chiefs Reserves | W | 2-4 |
| South Africa Diski Challenge | 2020/01/26 10:05 | Mamelodi Sundowns Reserves v Kaizer Chiefs Reserves | L | 4-3 |
| South Africa Diski Challenge | 2020/01/19 09:55 | Kaizer Chiefs Reserves v Supersport United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/01/12 10:04 | Highlands Park Reserves v Kaizer Chiefs Reserves | W | 1-4 |
| South Africa Diski Challenge | 2019/12/16 13:00 | Polokwane City Reserves v Kaizer Chiefs Reserves | L | 2-0 |
| South Africa Diski Challenge | 2019/12/08 10:01 | Kaizer Chiefs Reserves v Golden Arrows Reserves | W | 5-1 |
| South Africa Diski Challenge | 2019/11/30 11:00 | Kaizer Chiefs Reserves v Maritzburg United Reserves | W | 3-0 |
| South Africa Diski Challenge | 2020/02/16 07:58 | Cape Town City FC Reserves v Stellenbosch FC Reserves | W | 3-1 |
| South Africa Diski Challenge | 2020/02/09 08:00 | Cape Town City FC Reserves v Supersport United Reserves | L | 1-4 |
| South Africa Diski Challenge | 2020/01/19 08:04 | Cape Town City FC Reserves v Orlando Pirates Reserves | L | 0-1 |
| South Africa Diski Challenge | 2019/12/14 09:58 | Highlands Park Reserves v Cape Town City FC Reserves | W | 0-1 |
| South Africa Diski Challenge | 2019/12/08 08:00 | Cape Town City FC Reserves v Polokwane City Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/12/01 08:00 | Cape Town City FC Reserves v Baroka FC Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/11/24 07:59 | Supersport United Reserves v Cape Town City FC Reserves | L | 3-2 |
| South Africa Diski Challenge | 2019/11/17 07:59 | Stellenbosch FC Reserves v Cape Town City FC Reserves | W | 0-1 |