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