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| H (Match allé) | Tivoli Gardens | - | Cavalier FC | 0:1 | ||
| R (match retour) | Cavalier FC | - | Tivoli Gardens | 0:0 | ||
| H (Match allé): 25.09.2021 19:00 | R (match retour): 29.09.2021 21:30 | vainqueur: Cavalier FC | ||||
| H (Match allé) | Mount Pleasant Academy | - | Waterhouse FC | 0:1 | ||
| R (match retour) | Waterhouse FC | - | Mount Pleasant Academy | 1:1 | ||
| H (Match allé): 25.09.2021 21:30 | R (match retour): 29.09.2021 19:00 | vainqueur: Waterhouse FC | ||||
