| Sudáfrica - Diski Challenge | 2019/02/02 07:57 | Highlands Park - B v Chippa United - B | W | 4-1 |
| Sudáfrica - Diski Challenge | 2019/09/14 09:59 | Highlands Park - B v Stellenbosch FC - B | W | 3-1 |
| Sudáfrica - Diski Challenge | 2019/09/07 10:00 | Highlands Park - B v Orlando Pirates - B | W | 1-0 |
| Sudáfrica - Diski Challenge | 2019/08/31 10:01 | Mamelodi Sundowns - B v Highlands Park - B | L | 1-0 |
| Sudáfrica - Diski Challenge | 2019/08/25 08:00 | Highlands Park - B v Polokwane City - B | W | 3-1 |
| Sudáfrica - Diski Challenge | 2019/08/11 10:00 | Highlands Park - B v Baroka FC - B | L | 0-3 |
| South Africa Diski Shield | 2019/04/13 07:58 | Bidvest Wits - B v Highlands Park - B | L | 4-2 |
| Sudáfrica - Diski Challenge | 2019/04/07 09:58 | Orlando Pirates - B v Highlands Park - B | L | 2-1 |
| Sudáfrica - Diski Challenge | 2019/03/31 10:11 | Highlands Park - B v Kaizer Chiefs - B | L | 1-3 |
| Sudáfrica - Diski Challenge | 2019/09/24 10:00 | Chippa United - B v Orlando Pirates - B | L | 0-2 |
| Sudáfrica - Diski Challenge | 2019/09/07 08:02 | Supersport United - B v Chippa United - B | L | 4-0 |
| Sudáfrica - Diski Challenge | 2019/08/24 08:00 | Cape Town City FC - B v Chippa United - B | W | 0-3 |
| Sudáfrica - Diski Challenge | 2019/08/09 07:53 | Stellenbosch FC - B v Chippa United - B | L | 2-1 |
| Sudáfrica - Diski Challenge | 2019/02/02 07:57 | Highlands Park - B v Chippa United - B | L | 4-1 |
| Sudáfrica - Diski Challenge | 2019/01/26 07:59 | Amazulu - B v Chippa United - B | D | 0-0 |
| Sudáfrica - Diski Challenge | 2019/01/20 08:00 | Chippa United - B v Bidvest Wits - B | L | 0-2 |
| Sudáfrica - Diski Challenge | 2019/01/13 10:04 | Chippa United - B v Orlando Pirates - B | L | 1-2 |