| South Africa Diski Challenge | 2020/01/25 08:00 | Polokwane City Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/09/10 11:00 | Sekhukhune United Reserves v Polokwane City Reserves | L | 2-0 |
| South Africa Diski Challenge | 2020/03/15 08:00 | Black Leopards Reserves v Polokwane City Reserves | D | 1-1 |
| South Africa Diski Challenge | 2020/02/29 08:00 | Polokwane City Reserves v Supersport United Reserves | W | 1-0 |
| South Africa Diski Challenge | 2020/02/23 08:00 | Amazulu Reserves v Polokwane City Reserves | L | 1-0 |
| South Africa Diski Challenge | 2020/02/15 08:00 | Polokwane City Reserves v Bloem Celtic Reserves | L | 0-1 |
| South Africa Diski Challenge | 2020/02/09 08:07 | Golden Arrows Reserves v Polokwane City Reserves | L | 4-3 |
| South Africa Diski Challenge | 2020/02/01 07:59 | Polokwane City Reserves v Highlands Park Reserves | L | 0-1 |
| South Africa Diski Challenge | 2020/01/25 08:00 | Polokwane City Reserves v Chippa United Reserves | D | 1-1 |
| South Africa Diski Challenge | 2023/09/09 08:00 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/04/29 08:00 | TS Galaxy Reserves v Chippa United Reserves | L | 2-0 |
| South Africa Diski Challenge | 2023/04/16 08:00 | Royal AM Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/04/01 10:00 | Stellenbosch FC Reserves v Chippa United Reserves | L | 2-1 |
| South Africa Diski Challenge | 2023/03/12 08:00 | Supersport United Reserves v Chippa United Reserves | L | 5-2 |
| South Africa Diski Challenge | 2023/02/19 08:00 | Moroka Swallows Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2023/01/29 08:00 | Maritzburg United Reserves v Chippa United Reserves | L | 1-0 |
| South Africa Diski Challenge | 2023/01/22 10:00 | Richards Bay FC Reserves v Chippa United Reserves | L | 3-1 |