CONCACAF Gold Cup 2025, Final tournament, Group D |
 | 15.06.2025 |  | USA | – | Trinidad and Tobago |  | 5:0 (3:0) |
| San José |
CONCACAF Gold Cup 2023, Final tournament, Group A |
| 02.07.2023 | | USA | – | Trinidad and Tobago | | 6:0 (3:0) |
| Charlotte |
CONCACAF Gold Cup 2023, Final tournament, Group A |
| 28.06.2023 |  | Jamaica | – | Trinidad and Tobago | | 4:1 (3:0) |
| Saint Louis |
CONCACAF Gold Cup 2021, Final tournament, Group A |
| 14.07.2021 | | Trinidad and Tobago | – | El Salvador |  | 0:2 (0:1) |
| Frisco |
CONCACAF Gold Cup 2019, Final tournament, Group D |
| 22.06.2019 | | USA | – | Trinidad and Tobago | | 6:0 (1:0) |
| Cleveland |
CONCACAF Gold Cup 2019, Final tournament, Group D |
| 18.06.2019 |  | Panama | – | Trinidad and Tobago | | 2:0 (0:0) |
| Saint Paul |
CONCACAF Gold Cup 2013, Final tournament, Quarterfinal |
| 20.07.2013 |  | Mexico | – | Trinidad and Tobago | | 1:0 (0:0) |
| Atlanta |
CONCACAF Gold Cup 2013, Final tournament, Group B |
| 12.07.2013 | | Trinidad and Tobago | – | Haiti |  | 0:2 (0:1) |
| Miami |
CONCACAF Gold Cup 2007, Final tournament, Group B |
| 09.06.2007 | | USA | – | Trinidad and Tobago | | 2:0 (1:0) |
| Carson |
CONCACAF Gold Cup 2007, Final tournament, Group B |
| 07.06.2007 | | El Salvador | – | Trinidad and Tobago | | 2:1 (1:1) |
| Carson |
CONCACAF Gold Cup 2005, Final tournament, Group A |
| 12.07.2005 |  | Colombia | – | Trinidad and Tobago | | 2:0 (0:0) |
| Miami |
CONCACAF Gold Cup 2003, Qualifying tournament, Playoff |
| 25.04.2003 | | Trinidad and Tobago | – | Honduras |  | 0:2 (0:1) |
| Fort-de-France |
CONCACAF Gold Cup 2003, Qualifying tournament, Playoff |
| 23.04.2003 |  | Martinique | – | Trinidad and Tobago | | 3:2 (0:2) |
| Fort-de-France |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, Final Round, Group B |
| 30.03.2003 | | Trinidad and Tobago | – | Cuba |  | 1:3 (1:1) |
| San Fernando |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, First Round, Group A |
| 17.11.2002 | | Trinidad and Tobago | – | Saint Lucia |  | 0:1 (0:0) |
| Macoya |
CONCACAF Gold Cup 2002, Final tournament, Group C |
| 22.01.2002 | | Trinidad and Tobago | – | Martinique | | 0:1 (0:0) |
| Miami |
CONCACAF Gold Cup 2000, Final tournament, Semifinal |
| 24.02.2000 | | Trinidad and Tobago | – | Canada |  | 0:1 (0:0) |
| Los Angeles |
CONCACAF Gold Cup 2000, Final tournament, Group C |
| 13.02.2000 | | Mexico | – | Trinidad and Tobago | | 4:0 (1:0) |
| San Diego |
CONCACAF Gold Cup 1998, Final tournament, Group B |
| 04.02.1998 | | Mexico | – | Trinidad and Tobago | | 4:2 (1:0) |
| Oakland |
CONCACAF Gold Cup 1996, Final tournament, Group C |
| 13.01.1996 | | USA | – | Trinidad and Tobago | | 3:2 (2:2) |
| Anaheim |
CONCACAF Gold Cup 1996, Final tournament, Group C |
| 10.01.1996 | | Trinidad and Tobago | – | El Salvador | | 2:3 (1:0) |
| Anaheim |
CONCACAF Gold Cup 1991, Final tournament, Group B |
| 03.07.1991 | | Trinidad and Tobago | – | Guatemala |  | 0:1 (0:0) |
| Los Angeles |
CONCACAF Gold Cup 1991, Final tournament, Group B |
| 29.06.1991 | | USA | – | Trinidad and Tobago | | 2:1 (0:0) |
| Pasadena |
CONCACAF Championship 1989, Final tournament, Final Round |
| 18.11.1989 | | Trinidad and Tobago | – | USA | | 0:1 (0:1) |
| Port of Spain |
CONCACAF Championship 1989, Final tournament, Final Round |
| 11.06.1989 |  | Costa Rica | – | Trinidad and Tobago | | 1:0 (0:0) |
| San José |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
| 19.05.1985 | | USA | – | Trinidad and Tobago | | 1:0 (1:0) |
| Torrens |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
| 15.05.1985 | | USA | – | Trinidad and Tobago | | 2:1 (1:1) |
| Saint Louis |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
| 24.04.1985 | | Costa Rica | – | Trinidad and Tobago | | 3:0 (1:0) |
| San José |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 01.08.1980 | | Haiti | – | Trinidad and Tobago | | 2:0 (0:0) |
| Port-au-Prince |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 2 |
| 18.12.1976 |  | Suriname | – | Trinidad and Tobago | | 3:2 (0:1) * |
| French Guiana, Cayenne |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 15.08.1976 |  | Barbados | – | Trinidad and Tobago | | 2:1 (0:0) |
| Bridgetown |
CONCACAF Championship 1973, Final tournament, Final Round |
| 04.12.1973 | | Haiti | – | Trinidad and Tobago | | 2:1 (1:1) |
| Port-au-Prince |
CONCACAF Championship 1973, Final tournament, Final Round |
| 29.11.1973 | | Honduras | – | Trinidad and Tobago | | 2:1 (1:0) |
| Port-au-Prince |
CONCACAF Championship 1971, Final tournament, Final Round |
| 05.12.1971 | | Trinidad and Tobago | – | Haiti | | 0:6 |
| Port of Spain |
CONCACAF Championship 1971, Final tournament, Final Round |
| 26.11.1971 | | Trinidad and Tobago | – | Mexico | | 0:2 |
| Port of Spain |
CONCACAF Championship 1969, Final tournament, Final Round |
| 04.12.1969 | | Costa Rica | – | Trinidad and Tobago | | 5:0 (1:0) |
| San José |
CONCACAF Championship 1969, Final tournament, Final Round |
| 02.12.1969 |  | Netherlands Antilles | – | Trinidad and Tobago | | 3:1 (1:1) |
| San José |
CONCACAF Championship 1969, Final tournament, Final Round |
| 27.11.1969 | | Guatemala | – | Trinidad and Tobago | | 2:0 (1:0) |
| San José |
CONCACAF Championship 1967, Final tournament, Final Round |
| 14.03.1967 | | Guatemala | – | Trinidad and Tobago | | 2:0 (1:0) |
| Tegucigalpa |
CONCACAF Championship 1967, Final tournament, Final Round |
| 12.03.1967 | | Mexico | – | Trinidad and Tobago | | 4:0 (2:0) |
| Tegucigalpa |
CONCACAF Championship 1967, Final tournament, Final Round |
| 05.03.1967 | | Honduras | – | Trinidad and Tobago | | 1:0 (1:0) |
| Tegucigalpa |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 11.01.1967 | | Haiti | – | Trinidad and Tobago | | 4:2 |
| Kingston |
