Caribbean Championship 2017, Qualifying tournament, Fifth place playoff |
 | 08.01.2017 | | Haiti | – | Trinidad and Tobago | | 4:3 aet
(2:2, 2:2) |
| Couva |
Caribbean Championship 2017, Qualifying tournament, Fifth place playoff |
| 04.01.2017 | | Trinidad and Tobago | – | Suriname | | 1:2 aet
(0:0, 1:1) |
| Couva |
Caribbean Championship 2017, Qualifying tournament, Third round, group 4 |
| 11.10.2016 | | Martinique | – | Trinidad and Tobago | | 2:0 aet
(0:0) |
| Fort-de-France |
Caribbean Championship 2012, Final tournament, Final |
| 16.12.2012 | | Cuba | – | Trinidad and Tobago | | 1:0 aet
(0:0) |
| St. John's |
Caribbean Championship 2012, Final tournament, Group A |
| 09.12.2012 | | Antigua and Barbuda | – | Trinidad and Tobago | | 2:0 (0:0) |
| St. John's |
Caribbean Championship 2010, Final tournament, Group H |
| 28.11.2010 | | Grenada | – | Trinidad and Tobago | | 1:0 (0:0) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group H |
| 26.11.2010 | | Trinidad and Tobago | – | Cuba | | 0:2 (0:1) |
| Fort-de-France |
Caribbean Championship 2008, Final tournament, Group A |
| 03.12.2008 | | Trinidad and Tobago | – | Grenada | | 1:2 (0:1) |
| Kingston |
Caribbean Cup 2007, Final tournament, Final |
| 23.01.2007 | | Trinidad and Tobago | – | Haiti | | 1:2 (0:1) |
| Port of Spain |
Caribbean Cup 2005, Final tournament, Final Round |
| 22.02.2005 | | Trinidad and Tobago | – | Cuba | | 1:2 (1:1) |
| Bridgetown |
Caribbean Cup 2005, Final tournament, Final Round |
| 20.02.2005 | | Jamaica | – | Trinidad and Tobago | | 2:1 (2:1) |
| Bridgetown |
Caribbean Cup 2005, Qualifying tournament, Third round |
| 16.01.2005 | | Saint Vincent and Grenadines | – | Trinidad and Tobago | | 1:0 (0:0) |
| Kingstown |
Caribbean Cup 2001, Final tournament, Group 1 |
| 19.05.2001 | | Trinidad and Tobago | – | Martinique | | 1:2 (1:1) |
| Port of Spain |
Caribbean Cup 1998, Final tournament, Final |
| 31.07.1998 | | Trinidad and Tobago | – | Jamaica | | 1:2 (0:2) |
| Trinidad and Tobago |
Caribbean Cup 1997, Final tournament, Group B |
| 04.07.1997 | | Trinidad and Tobago | – | Martinique | | 1:2 (1:1) |
| Bassterre |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
| 06.04.1997 | | Trinidad and Tobago | – | Grenada | | 2:3 (0:2) |
| Port of Spain |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
| 04.04.1997 | | Trinidad and Tobago | – | Barbados | | 0:1 (0:1) |
| Port of Spain |
Caribbean Cup 1995, Final tournament, Group B |
| 23.07.1995 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
Caribbean Cup 1993, Final tournament, Semifinal |
| 28.05.1993 | | Jamaica | – | Trinidad and Tobago | | 3:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group B |
| 25.05.1993 | | Martinique | – | Trinidad and Tobago | | 3:2 |
| Montego Bay |
Caribbean Cup 1991, Final tournament, Final |
| 02.06.1991 | | Jamaica | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kingston |
Caribbean Cup 1991, Final tournament, Group B |
| 23.05.1991 | | Trinidad and Tobago | – | Saint Lucia | | 1:2 |
| Kingston |
Caribbean Cup 1989, Final tournament, Group A |
| 07.07.1989 | | Trinidad and Tobago | – | Guadeloupe | | 0:2 |
| Bridgetown |
Caribbean Cup 1989, Qualifying tournament, Zone A |
| 06.06.1989 | | Grenada | – | Trinidad and Tobago | | 1:0 |
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