series
| Sept. 1, 2009 | TRI1 | 2009 | 11 | South End | 1 - 4 | United Petrotrin | 1 | |
| Aug. 1, 2009 | TRI1 | 2009 | 15 | South End | 2 - 2 | United Petrotrin | 1 |
scoreboard
| TRI1 | 2009 | 20 | Defence Force | 0 - 1 | San Juan Jabloteh | 1 |
| Sept. 1, 2009 | TRI1 | 2009 | 11 | South End | 1 - 4 | United Petrotrin | 1 | |
| Aug. 1, 2009 | TRI1 | 2009 | 15 | South End | 2 - 2 | United Petrotrin | 1 |
| TRI1 | 2009 | 20 | Defence Force | 0 - 1 | San Juan Jabloteh | 1 |