CONCACAF Gold Cup 2025, Qualifying tournament, Qualifying Round |
 | 25.03.2025 |  | Trinidad and Tobago | – | Cuba |  | 4:0 (2:0) |
| Couva |
CONCACAF Gold Cup 2025, Qualifying tournament, Qualifying Round |
| 21.03.2025 | | Cuba | – | Trinidad and Tobago | | 1:2 (1:1) |
| Santiago de Cuba |
CONCACAF Gold Cup 2023, Final tournament, Group A |
| 25.06.2023 | | Trinidad and Tobago | – | Saint Kitts and Nevis |  | 3:0 (1:0) |
| Fort Lauderdale |
CONCACAF Gold Cup 2021, Qualifying tournament, First Round |
| 02.07.2021 | | Trinidad and Tobago | – | Montserrat |  | 6:1 (3:0) |
| Fort Lauderdale |
CONCACAF Gold Cup 2015, Final tournament, Group C |
| 12.07.2015 | | Trinidad and Tobago | – | Cuba | | 2:0 (2:0) |
| USA, Glendale |
CONCACAF Gold Cup 2015, Final tournament, Group C |
| 09.07.2015 | | Trinidad and Tobago | – | Guatemala |  | 3:1 (3:0) |
| USA, Chicago |
CONCACAF Gold Cup 2013, Final tournament, Group B |
| 15.07.2013 |  | Honduras | – | Trinidad and Tobago | | 0:2 (0:0) |
| Houston |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, Final Round, Group B |
| 28.03.2003 | | Trinidad and Tobago | – | Guadeloupe |  | 1:0 (0:0) |
| Macoya |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, Final Round, Group B |
| 26.03.2003 | | Trinidad and Tobago | – | Antigua and Barbuda |  | 2:0 (1:0) |
| Port of Spain |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, First Round, Group A |
| 15.11.2002 | | Trinidad and Tobago | – | Saint Kitts and Nevis | | 2:0 (1:0) |
| Port of Spain |
CONCACAF Gold Cup 2000, Final tournament, Quarterfinal |
| 20.02.2000 |  | Costa Rica | – | Trinidad and Tobago | | 1:2 aet
(0:1, 1:1) |
| San Diego |
CONCACAF Gold Cup 2000, Final tournament, Group C |
| 15.02.2000 | | Trinidad and Tobago | – | Guatemala | | 4:2 (2:1) |
| Los Angeles |
CONCACAF Gold Cup 1998, Final tournament, Group B |
| 01.02.1998 | | Honduras | – | Trinidad and Tobago | | 1:3 (0:2) |
| Oakland |
CONCACAF Gold Cup 1991, Final tournament, Group B |
| 01.07.1991 | | Costa Rica | – | Trinidad and Tobago | | 1:2 (1:1) |
| Pasadena |
CONCACAF Championship 1989, Final tournament, Final Round |
| 03.09.1989 | | Trinidad and Tobago | – | Guatemala | | 2:1 (1:1) |
| Port of Spain |
CONCACAF Championship 1989, Final tournament, Final Round |
| 20.08.1989 | | Guatemala | – | Trinidad and Tobago | | 0:1 (0:0) |
| Ciudad de Guatemala |
CONCACAF Championship 1989, Final tournament, Final Round |
| 30.07.1989 | | Trinidad and Tobago | – | El Salvador |  | 2:0 (0:0) |
| Port of Spain |
CONCACAF Championship 1989, Qualifying tournament, First Round |
| 08.05.1988 | | Trinidad and Tobago | – | Guyana |  | 1:0 (0:0) |
| Port of Spain |
CONCACAF Championship 1989, Qualifying tournament, First Round |
| 17.04.1988 | | Guyana | – | Trinidad and Tobago | | 0:4 (0:2) |
| Georgetown |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 17.08.1980 | | Trinidad and Tobago | – | Haiti |  | 1:0 (0:0) |
| San Fernando |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 14.09.1976 |  | Barbados | – | Trinidad and Tobago | | 1:3 (1:1) * |
| Bridgetown |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 31.08.1976 | | Trinidad and Tobago | – | Barbados | | 1:0 (1:0) |
| Port of Spain |
CONCACAF Championship 1973, Final tournament, Final Round |
| 17.12.1973 | | Trinidad and Tobago | – | Netherlands Antilles |  | 4:0 (2:0) |
| Port-au-Prince |
CONCACAF Championship 1973, Final tournament, Final Round |
| 14.12.1973 | | Trinidad and Tobago | – | Mexico |  | 4:0 (2:0) |
| Port-au-Prince |
CONCACAF Championship 1973, Final tournament, Final Round |
| 10.12.1973 | | Trinidad and Tobago | – | Guatemala | | 1:0 (1:0) |
| Port-au-Prince |
CONCACAF Championship 1973, Qualifying tournament, Caribbean Zone, group 6 |
| 28.11.1972 | | Trinidad and Tobago | – | Dutch Guiana |  | 2:1 (0:0) |
| Port of Spain |
CONCACAF Championship 1973, Qualifying tournament, Caribbean Zone, group 6 |
| 19.11.1972 |  | Antigua | – | Trinidad and Tobago | | 1:2 (0:2) |
| St. John's |
CONCACAF Championship 1973, Qualifying tournament, Caribbean Zone, group 6 |
| 10.11.1972 | | Trinidad and Tobago | – | Antigua | | 11:1 (4:1) |
| Port of Spain |
CONCACAF Championship 1971, Final tournament, Final Round |
| 29.11.1971 | | Trinidad and Tobago | – | Costa Rica | | 3:1 |
| Port of Spain |
CONCACAF Championship 1969, Final tournament, Final Round |
| 30.11.1969 | | Trinidad and Tobago | – | Jamaica |  | 3:2 (2:2) |
| San José |
CONCACAF Championship 1967, Final tournament, Final Round |
| 17.03.1967 | | Trinidad and Tobago | – | Nicaragua |  | 3:1 (1:0) |
| Tegucigalpa |
CONCACAF Championship 1967, Final tournament, Final Round |
| 08.03.1967 | | Trinidad and Tobago | – | Haiti | | 3:2 (2:1) |
| Tegucigalpa |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 24.01.1967 | | Trinidad and Tobago | – | Netherlands Antilles | | 2:0 |
| Kingston |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 21.01.1967 | | Trinidad and Tobago | – | Cuba | | 2:1 |
| Kingston |
CONCACAF Championship 1985, Qualifying tournament, First Round |
| | | Trinidad and Tobago | – | Grenada |  | +:- |
| |
CONCACAF Championship 1969, Qualifying tournament, Qualifying round |
| | | Trinidad and Tobago | – | El Salvador | | +:- |
| |
