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| 02.10.2021 | ||||
| 21:45 | D1F Final Play-Off | Waterhouse FC | 1-1/p.4-5 | Cavalier FC |
| 19:00 | D1PO 3dr Place | Mount Pleasant | 1-1/p.3-4 | Tivoli Gardens |
| 29.09.2021 | ||||
| 21:50 | D1PO Semifinal Play-Off | Cavalier FC | 0-0 | Tivoli Gardens |
| 19:00 | D1PO Semifinal Play-Off | Waterhouse FC | 1-1 | Mount Pleasant |
| 25.09.2021 | ||||
| 21:30 | D1PO Semifinal Play-Off | Mount Pleasant | 0-1 | Waterhouse FC |
| 19:00 | D1PO Semifinal Play-Off | Tivoli Gardens | 0-1 | Cavalier FC |
| 22.09.2021 | ||||
| 21:30 | D1PO Quarterfinal Play-Off | Mount Pleasant | 1-1 | Harbour View |
| 19:00 | D1PO Quarterfinal Play-Off | Tivoli Gardens | 4-0 | Vere United |
| 18.09.2021 | ||||
| 21:30 | D1PO Quarterfinal Play-Off | Vere United | 0-0 | Tivoli Gardens |
| 19:00 | D1PO Quarterfinal Play-Off | Harbour View | 1-3 | Mount Pleasant |
| 11.09.2021 | ||||
| 21:30 | D1 Regular Season | Vere United | 0-1 | Cavalier FC |
| 19:00 | D1 Regular Season | Tivoli Gardens | 1-1 | Molynes United |