| Zuid-Afrika - Diski Challenge | 2018/09/08 10:00 | Highlands Park Reserves v Cape Town City FC - Reserves | W | 0-3 |
| Zuid-Afrika - Diski Challenge | 2019/10/13 10:00 | Bloem Celtic - Reserves v Cape Town City FC - Reserves | L | 5-0 |
| Zuid-Afrika - Diski Challenge | 2019/09/28 07:58 | Orlando Pirates - Reserves v Cape Town City FC - Reserves | W | 2-3 |
| Zuid-Afrika - Diski Challenge | 2019/09/24 13:00 | Cape Town City FC - Reserves v Kaizer Chiefs - Reserves | L | 2-4 |
| Zuid-Afrika - Diski Challenge | 2019/09/14 08:00 | Maritzburg United - Reserves v Cape Town City FC - Reserves | W | 0-2 |
| Zuid-Afrika - Diski Challenge | 2019/09/07 07:57 | Polokwane City - Reserves v Cape Town City FC - Reserves | W | 2-3 |
| Zuid-Afrika - Diski Challenge | 2019/08/24 08:00 | Cape Town City FC - Reserves v Chippa United - Reserves | L | 0-3 |
| Zuid-Afrika - Diski Shield | 2019/04/13 08:00 | Cape Town City FC - Reserves v Bloem Celtic - Reserves | D | 1-1 |
| Zuid-Afrika - Diski Challenge | 2019/03/31 09:27 | Cape Town City FC - Reserves v Supersport United - Reserves | L | 1-2 |
| Zuid-Afrika - Diski Challenge | 2019/10/19 09:59 | Highlands Park Reserves v Maritzburg United - Reserves | D | 1-1 |
| Zuid-Afrika - Diski Challenge | 2019/10/12 10:00 | Highlands Park Reserves v Black Leopards - Reserves | W | 1-0 |
| Zuid-Afrika - Diski Challenge | 2019/10/06 08:00 | Golden Arrows - Reserves v Highlands Park Reserves | W | 0-4 |
| Zuid-Afrika - Diski Challenge | 2019/09/28 08:12 | Highlands Park Reserves v Chippa United - Reserves | D | 1-1 |
| Zuid-Afrika - Diski Challenge | 2019/09/14 09:59 | Highlands Park Reserves v Stellenbosch FC - Reserves | W | 3-1 |
| Zuid-Afrika - Diski Challenge | 2019/09/07 10:00 | Highlands Park Reserves v Orlando Pirates - Reserves | W | 1-0 |
| Zuid-Afrika - Diski Challenge | 2019/08/31 10:01 | Mamelodi Sundowns - Reserves v Highlands Park Reserves | L | 1-0 |
| Zuid-Afrika - Diski Challenge | 2019/08/25 08:00 | Highlands Park Reserves v Polokwane City - Reserves | W | 3-1 |