series
| Oct. 24, 2009 | TRI1 | 2009 | 26 | Caledonia AIA | 1 - 1 | Joe Public F.C. | 1 | |
| July 28, 2009 | TRI1 | 2009 | 14 | Caledonia AIA | 3 - 2 | Joe Public F.C. | 1 | |
| May 8, 2009 | TRI1 | 2009 | 1 | Caledonia AIA | 2 - 3 | Joe Public F.C. | 1 |
scoreboard
| CCL | 2009-2010 | pre | D.C. United | 1 - 1 | Luis Ángel Firpo | RFK Stadium | 1 |
| CCL | 2009-2010 | pre | CD Jalapa | 0 - 3 | Pachuca | Estadio Hidalgo | 0 |
| TRI1 | 2009 | 14 | Ma Pau | 2 - 0 | Tobago United | 1 | |
| TRI1 | 2009 | 14 | Police | 1 - 2 | St Ann's Rangers | 1 | |
| TRI1 | 2009 | 14 | Defence Force | 2 - 0 | South End | 1 |