| Südafrika - Diski Challenge | 2019/09/07 08:02 | Supersport United - Reserve v Chippa United - Reserve | L | 4-0 |
| Südafrika - Diski Challenge | 2018/12/02 07:59 | Supersport United - Reserve v Chippa United - Reserve | L | 1-0 |
| Südafrika - Diski Challenge | 2020/02/15 07:59 | Maritzburg United - Reserve v Chippa United - Reserve | D | 2-2 |
| Südafrika - Diski Challenge | 2020/02/09 07:00 | Amazulu - Reserve v Chippa United - Reserve | L | 2-1 |
| Südafrika - Diski Challenge | 2020/01/25 08:00 | Polokwane City - Reserve v Chippa United - Reserve | D | 1-1 |
| Südafrika - Diski Challenge | 2020/01/18 08:00 | Chippa United - Reserve v Mamelodi Sundowns - Reserve | W | 3-1 |
| Südafrika - Diski Challenge | 2020/01/12 08:00 | Golden Arrows - Reserve v Chippa United - Reserve | D | 4-4 |
| Südafrika - Diski Challenge | 2019/12/14 07:55 | Chippa United - Reserve v Stellenbosch FC - Reserve | W | 2-1 |
| Südafrika - Diski Challenge | 2019/12/07 08:00 | Orlando Pirates - Reserve v Chippa United - Reserve | L | 3-2 |
| Südafrika - Diski Challenge | 2019/11/30 08:01 | Chippa United - Reserve v Highlands Park - Reserve | L | 1-3 |
| Südafrika - Diski Challenge | 2020/02/15 08:02 | Supersport United - Reserve v Mamelodi Sundowns - Reserve | L | 1-2 |
| Südafrika - Diski Challenge | 2020/02/09 08:00 | Cape Town City FC - Reserve v Supersport United - Reserve | W | 1-4 |
| Südafrika - Diski Challenge | 2020/01/25 10:00 | Supersport United - Reserve v Orlando Pirates - Reserve | L | 0-3 |
| Südafrika - Diski Challenge | 2020/01/19 09:55 | Kaizer Chiefs - Reserve v Supersport United - Reserve | D | 1-1 |
| Südafrika - Diski Challenge | 2020/01/11 08:00 | Black Leopards - Reserve v Supersport United - Reserve | W | 0-1 |
| Südafrika - Diski Challenge | 2019/12/14 11:00 | Bidvest Wits - Reserve v Supersport United - Reserve | L | 3-2 |
| Südafrika - Diski Challenge | 2019/12/14 07:58 | Bidvest Wits - Reserve v Supersport United - Reserve | L | 3-2 |
| Südafrika - Diski Challenge | 2019/12/07 07:57 | Stellenbosch FC - Reserve v Supersport United - Reserve | D | 1-1 |