| 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 |
| South Africa Diski Challenge | 2019/11/03 10:00 | Cape Town City FC Reserves v Bidvest Wits Reserves | L | 1-2 |
| South Africa Diski Challenge | 2019/10/27 09:59 | Cape Town City FC Reserves v Highlands Park Reserves | W | 2-1 |
| South Africa Diski Challenge | 2019/10/13 10:00 | Siwelele FC Reserves v Cape Town City FC Reserves | L | 5-0 |
| South Africa Diski Challenge | 2019/09/28 07:58 | Orlando Pirates Reserves v Cape Town City FC Reserves | W | 2-3 |
| South Africa Diski Challenge | 2019/12/08 08:00 | Siwelele FC Reserves v Black Leopards Reserves | L | 3-1 |
| South Africa Diski Challenge | 2019/12/01 08:00 | Black Leopards Reserves v Golden Arrows Reserves | L | 1-4 |
| South Africa Diski Challenge | 2019/11/17 07:58 | Black Leopards Reserves v Chippa United Reserves | D | 2-2 |
| South Africa Diski Challenge | 2019/10/26 09:59 | Baroka FC Reserves v Black Leopards Reserves | L | 1-0 |
| South Africa Diski Challenge | 2019/10/20 08:01 | Black Leopards Reserves v Siwelele FC Reserves | D | 4-4 |
| South Africa Diski Challenge | 2019/10/12 10:00 | Highlands Park Reserves v Black Leopards Reserves | L | 1-0 |
| South Africa Diski Challenge | 2019/10/05 07:58 | Black Leopards Reserves v Mamelodi Sundowns Reserves | L | 0-2 |
| South Africa Diski Challenge | 2019/09/29 08:00 | Kaizer Chiefs Reserves v Black Leopards Reserves | D | 0-0 |