| Zuid-Afrika - Diski Challenge | 2022/10/09 08:00 | Cape Town City FC - Reserves v Chippa United - Reserves | W | 3-1 |
| Zuid-Afrika - Diski Challenge | 2022/04/24 08:00 | Cape Town City FC - Reserves v Chippa United - Reserves | L | 1-3 |
| Zuid-Afrika - Diski Challenge | 2019/08/24 08:00 | Cape Town City FC - Reserves v Chippa United - Reserves | L | 0-3 |
| Zuid-Afrika - Diski Challenge | 2018/11/18 08:01 | Cape Town City FC - Reserves v Chippa United - Reserves | W | 3-2 |
| Zuid-Afrika - Diski Challenge | 2024/03/17 08:00 | Amazulu - Reserves v Cape Town City FC - Reserves | L | 3-2 |
| Zuid-Afrika - Diski Challenge | 2024/03/10 08:00 | Cape Town City FC - Reserves v Polokwane City - Reserves | W | 6-1 |
| Zuid-Afrika - Diski Challenge | 2024/03/02 08:00 | Mamelodi Sundowns - Reserves v Cape Town City FC - Reserves | L | 3-2 |
| Zuid-Afrika - Diski Challenge | 2024/02/25 08:00 | Cape Town City FC - Reserves v Sekhukhune United - Reserves | W | 3-1 |
| Zuid-Afrika - Diski Challenge | 2024/02/18 08:00 | Cape Town City FC - Reserves v Richards Bay FC - Reserves | W | 2-1 |
| Zuid-Afrika - Diski Challenge | 2024/02/10 08:00 | Moroka Swallows - Reserves v Cape Town City FC - Reserves | D | 0-0 |
| Zuid-Afrika - Diski Challenge | 2024/02/04 08:00 | Cape Town City FC - Reserves v TS Galaxy - Reserves | W | 3-0 |
| Zuid-Afrika - Diski Challenge | 2024/01/28 09:00 | Cape Town City FC - Reserves v Mamelodi Sundowns - Reserves | L | 0-2 |
| Zuid-Afrika - Diski Challenge | 2024/03/09 08:00 | Royal AM - Reserves v Chippa United - Reserves | L | 5-2 |
| Zuid-Afrika - Diski Challenge | 2024/02/24 08:00 | Supersport United - Reserves v Chippa United - Reserves | L | 4-1 |
| Zuid-Afrika - Diski Challenge | 2024/02/17 08:00 | Chippa United - Reserves v Amazulu - Reserves | L | 0-3 |
| Zuid-Afrika - Diski Challenge | 2024/02/10 08:00 | Richards Bay FC - Reserves v Chippa United - Reserves | W | 1-3 |
| Zuid-Afrika - Diski Challenge | 2024/01/27 09:00 | Amazulu - Reserves v Chippa United - Reserves | W | 1-3 |
| Zuid-Afrika - Diski Challenge | 2024/01/13 11:00 | Kaizer Chiefs - Reserves v Chippa United - Reserves | D | 2-2 |
| Zuid-Afrika - Diski Challenge | 2023/11/11 08:00 | Moroka Swallows - Reserves v Chippa United - Reserves | W | 1-2 |
| Zuid-Afrika - Diski Challenge | 2023/10/29 08:00 | Sekhukhune United - Reserves v Chippa United - Reserves | L | 4-2 |