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GMT 02:00
| 13.05.2025 | |||
| 04:00 | Montego Bay Utd | 1-1 | Tivoli Gardens |
| 01:00 | Cavalier FC | 1-0 AET | Portmore United |
| 10.05.2025 | |||
| 03:00 | Portmore United | 1-1 | Cavalier FC |
| 01:00 | Tivoli Gardens | 1-2 | Montego Bay Utd |
| 04.05.2025 | |||
| 22:30 | Arnett Gardens | 5-1 | Harbour View |
| 22:30 | Cavalier FC | 4-3 | Molynes United |
| 22:30 | Humble Lions | 0-4 | Mount Pleasant |
| 22:30 | Portmore United | 2-0 | Racing United FC |
| 22:30 | Tivoli Gardens | 2-1 | Montego Bay Utd |
| 22:30 | Vere United | 1-3 | Chapelton Maroons FC |
| 22:30 | Waterhouse FC | 2-0 | Dunbeholden FC |
| 27.04.2025 | |||
| 22:30 | Chapelton Maroons FC | 2-2 | Tivoli Gardens |
| 16.05.2025 | ||||
| 00:00 | Cavalier FC | - | Arnett Gardens | |
| 03:00 | Montego Bay Utd | - | Mount Pleasant | |
| 19.05.2025 | ||||
| 00:00 | Mount Pleasant | - | Montego Bay Utd | |
| 03:00 | Arnett Gardens | - | Cavalier FC | |
| 23.05.2025 | ||||
| 22:59 | Loser Semi-Final 1 | - | Loser Semi-Final 2 | |
| 22:59 | Winner Semi-Final 1 | - | Winner Semi-Final 2 | |
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