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| H (Match allé) | Harbour View | - | Mount Pleasant Academy | 1:3 | ||
| R (match retour) | Mount Pleasant Academy | - | Harbour View | 1:1 (0:1) | ||
| H (Match allé): 18.09.2021 19:00 | R (match retour): 22.09.2021 21:30 | vainqueur: Mount Pleasant Academy | ||||
| H (Match allé) | Vere United | - | Tivoli Gardens | 0:0 | ||
| R (match retour) | Tivoli Gardens | - | Vere United | 4:0 | ||
| H (Match allé): 18.09.2021 21:30 | R (match retour): 22.09.2021 19:00 | vainqueur: Tivoli Gardens | ||||
