CONCACAF Gold Cup 2021, Final tournament, Group A |
 | 18.07.2021 |  | Guatemala | – | Trinidad and Tobago |  | 1:1 (0:1) |
| Frisco |
CONCACAF Gold Cup 2021, Final tournament, Group A |
| 10.07.2021 |  | Mexico | – | Trinidad and Tobago | | 0:0 |
| Arlington |
CONCACAF Gold Cup 2021, Qualifying tournament, Second round |
| 06.07.2021 | | Trinidad and Tobago | – | French Guiana |  | 1:1 (1:1),
pen. 8:7 |
| Fort Lauderdale |
CONCACAF Gold Cup 2019, Final tournament, Group D |
| 26.06.2019 | | Trinidad and Tobago | – | Guyana |  | 1:1 (0:0) |
| Kansas City |
CONCACAF Gold Cup 2015, Final tournament, Quarterfinal |
| 19.07.2015 | | Trinidad and Tobago | – | Panama |  | 1:1 aet
(0:1, 1:1),
pen. 5:6 |
| USA, East Rutherford |
CONCACAF Gold Cup 2015, Final tournament, Group C |
| 15.07.2015 | | Mexico | – | Trinidad and Tobago | | 4:4 (1:0) |
| USA, Charlotte |
CONCACAF Gold Cup 2013, Final tournament, Group B |
| 08.07.2013 |  | El Salvador | – | Trinidad and Tobago | | 2:2 (1:1) |
| Harrison |
CONCACAF Gold Cup 2007, Final tournament, Group B |
| 12.06.2007 | | Trinidad and Tobago | – | Guatemala | | 1:1 (0:0) |
| Foxborough |
CONCACAF Gold Cup 2005, Final tournament, Group A |
| 10.07.2005 | | Panama | – | Trinidad and Tobago | | 2:2 (1:1) |
| Miami |
CONCACAF Gold Cup 2005, Final tournament, Group A |
| 06.07.2005 | | Trinidad and Tobago | – | Honduras |  | 1:1 (1:1) |
| Miami |
CONCACAF Gold Cup 2002, Final tournament, Group C |
| 20.01.2002 |  | Costa Rica | – | Trinidad and Tobago | | 1:1 (0:0) |
| Miami |
CONCACAF Championship 1989, Final tournament, Final Round |
| 13.08.1989 | | El Salvador | – | Trinidad and Tobago | | 0:0 |
| Honduras, Tegucigalpa |
CONCACAF Championship 1989, Final tournament, Final Round |
| 28.05.1989 | | Trinidad and Tobago | – | Costa Rica | | 1:1 (0:0) |
| Port of Spain |
CONCACAF Championship 1989, Final tournament, Final Round |
| 13.05.1989 |  | USA | – | Trinidad and Tobago | | 1:1 (0:0) |
| Torrens |
CONCACAF Championship 1989, Qualifying tournament, Second round |
| 13.11.1988 | | Honduras | – | Trinidad and Tobago | | 1:1 (0:0) |
| Tegucigalpa |
CONCACAF Championship 1989, Qualifying tournament, Second round |
| 30.10.1988 | | Trinidad and Tobago | – | Honduras | | 0:0 |
| Port of Spain |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
| 28.04.1985 | | Costa Rica | – | Trinidad and Tobago | | 1:1 (0:1) |
| San José |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 29.11.1980 |  | Netherlands Antilles | – | Trinidad and Tobago | | 0:0 |
| Willemstad |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 09.11.1980 | | Trinidad and Tobago | – | Netherlands Antilles | | 0:0 |
| Port of Spain |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 2 |
| 28.11.1976 | | Trinidad and Tobago | – | Suriname |  | 2:2 (1:1) |
| Port of Spain |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 2 |
| 14.11.1976 | | Suriname | – | Trinidad and Tobago | | 1:1 (1:1) |
| Paramaribo |
CONCACAF Championship 1973, Qualifying tournament, Caribbean Zone, group 6 |
| 30.11.1972 | | Trinidad and Tobago | – | Dutch Guiana |  | 1:1 (0:0) |
| San Fernando |
CONCACAF Championship 1971, Final tournament, Final Round |
| 01.12.1971 | | Trinidad and Tobago | – | Honduras | | 1:1 |
| Port of Spain |
CONCACAF Championship 1971, Final tournament, Final Round |
| 20.11.1971 | | Trinidad and Tobago | – | Cuba |  | 2:2 |
| Port of Spain |
CONCACAF Championship 1969, Final tournament, Final Round |
| 07.12.1969 | | Mexico | – | Trinidad and Tobago | | 0:0 |
| San José |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 18.01.1967 |  | Jamaica | – | Trinidad and Tobago | | 1:1 |
| Kingston |
