series
| Aug. 12, 2006 | TRI1 | 2006 | 19 | Caledonia AIA | 1 - 2 | Defence Force | 1 | |
| June 6, 2006 | TRI1 | 2006 | 10 | Caledonia AIA | 2 - 1 | Defence Force | 1 | |
| April 8, 2006 | TRI1 | 2006 | 1 | Caledonia AIA | 1 - 0 | Defence Force | 1 |
scoreboard
| TRI1 | 2006 | 10 | San Juan Jabloteh | 1 - 0 | Strikers | 1 | |
| TRI1 | 2006 | 10 | St Ann's Rangers | 1 - 0 | Tobago United | 1 | |
| TRI1 | 2006 | 10 | United Petrotrin | 0 - 1 | W Connection | 1 | |
| TRI1 | 2006 | 10 | Joe Public F.C. | 0 - 0 | NE Stars | 1 |