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| 1st(1st leg) | Harbour View | - | Mount Pleasant Academy | 1:3 | ||
| 2nd (2nd leg) | Mount Pleasant Academy | - | Harbour View | 1:1 (0:1) | ||
| 1st(1st leg): 18/09/2021 18:00 | 2nd (2nd leg): 22/09/2021 20:30 | Winner: Mount Pleasant Academy | ||||
| 1st(1st leg) | Vere United | - | Tivoli Gardens | 0:0 | ||
| 2nd (2nd leg) | Tivoli Gardens | - | Vere United | 4:0 | ||
| 1st(1st leg): 18/09/2021 20:30 | 2nd (2nd leg): 22/09/2021 18:00 | Winner: Tivoli Gardens | ||||
