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National teams
National Premier League .:. Fixtures
| 17. Round | |||||
| 07/01/2009 | 15:30 | Village United | - | Sporting Central | _:_ |
| 07/01/2009 | 15:30 | St. Georges FC | - | Portmore United | _:_ |
| 07/01/2009 | 15:30 | Reno United | - | Waterhouse FC | _:_ |
| 07/01/2009 | 15:30 | Meadhaven United | - | Boys' Town | _:_ |
| 07/01/2009 | 16:00 | Rivoli United | - | Tivoli Gardens | _:_ |
| 07/01/2009 | 17:00 | Arnett Gardens | - | Harbour View | _:_ |
| 18. Round | |||||
| 11/01/2009 | 15:30 | Meadhaven United | - | St. Georges FC | _:_ |
| 11/01/2009 | 15:30 | Reno United | - | Arnett Gardens | _:_ |
| 11/01/2009 | 15:30 | Sporting Central | - | Portmore United | _:_ |
National Premier League .:. Results
| 16. Round | |||||
| 04/01/2009 | 18:30 | Harbour View | - | Reno United | 0:0 |
| 04/01/2009 | 19:00 | Portmore United | - | Meadhaven United | 3:0 |
| 04/01/2009 | 15:30 | Sporting Central | - | St. Georges FC | 0:1 |
| 04/01/2009 | 15:30 | Boys' Town | - | Rivoli United | 1:0 |
| 04/01/2009 | 16:00 | Waterhouse FC | - | Village United | 1:1 |
| 04/01/2009 | 17:00 | Tivoli Gardens | - | Arnett Gardens | 1:2 |
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