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 | | +:- |
| |
Superclásico
Copa Newton
Copa Lipton
Copa Rosa
Copa Félix Bogado
Copa Carlos Dittborn
Copa Ramón Castilla
Copa Rio Branco
Copa Rodrigues Alves
Taça Bernardo O'Higgins
Copa Artigas
Copa Paz del Chaco
Copa del Pacífico
