The draw for the fixtures and dates of those fixtures were recently announced by the PSL. These dates are subject to change depending on outstanding issues pertaining to the winners of the GladAfrcia Championship.
| June | |||||
| Saturday 19 June 2021 | |||||
| PSL Play-off MD1 | CHIPPA UNITED | RICHARDS BAY FC | |||
| Tuesday 22 June 2021 | |||||
| PSL Play-off MD2 | ROYAL AM | CHIPPA UNITED | |||
| Thursday 24 June 2021 | |||||
| PSL Play-off MD3 | ROYAL AM | RICHARDS BAY FC | |||
| Saturday 26 June 2021 | |||||
| PSL Play-off MD4 | RICHARDS BAY FC | CHIPPA UNITED | |||
| Monday 28 June 2021 | |||||
| PSL Play-off MD5 | RICHARDS BAY FC | ROYAL AM | |||
| Wednesday 30 June 2021 | |||||
| PSL Play-off MD6 | CHIPPA UNITED | ROYAL AM | |||