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| 1st(1st leg) | Tivoli Gardens | - | Cavalier FC | 0:1 | ||
| 2nd (2nd leg) | Cavalier FC | - | Tivoli Gardens | 0:0 | ||
| 1st(1st leg): 25/09/2021 18:00 | 2nd (2nd leg): 29/09/2021 20:30 | Winner: Cavalier FC | ||||
| 1st(1st leg) | Mount Pleasant Academy | - | Waterhouse FC | 0:1 | ||
| 2nd (2nd leg) | Waterhouse FC | - | Mount Pleasant Academy | 1:1 | ||
| 1st(1st leg): 25/09/2021 20:30 | 2nd (2nd leg): 29/09/2021 18:00 | Winner: Waterhouse FC | ||||
