World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
 | 08.06.2024 |  | Bahamas | | Trinidad and Tobago |  | 1:7 (0:4) |
| Saint Kitts and Nevis, Bassterre SKNFA Technical Centre |
World Cup 2022, Qualifying tournament, CONCACAF, Group F |
 | 08.06.2021 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 2:0 (1:0) |
| Dominican Republic, Santo Domingo de Guzmán |
World Cup 2022, Qualifying tournament, CONCACAF, Group F |
 | 25.03.2021 |  | Trinidad and Tobago | | Guyana |  | 3:0 (3:0) |
| Dominican Republic, San Cristóbal |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
 | 10.10.2017 |  | Trinidad and Tobago | | USA |  | 2:1 (2:0) |
| Couva |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
 | 24.03.2017 |  | Trinidad and Tobago | | Panama |  | 1:0 (1:0) |
| Port of Spain |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
 | 29.03.2016 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 6:0 (1:0) |
| Port of Spain |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
 | 25.03.2016 |  | Saint Vincent and Grenadines | | Trinidad and Tobago |  | 2:3 (1:0) |
| Kingstown |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
 | 13.11.2015 |  | Guatemala | | Trinidad and Tobago |  | 1:2 (0:0) |
| Ciudad de Guatemala |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
 | 15.11.2011 |  | Trinidad and Tobago | | Guyana |  | 2:0 (0:0) |
| Port of Spain |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
 | 11.10.2011 |  | Trinidad and Tobago | | Barbados |  | 4:0 (1:0) |
| Port of Spain |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
 | 06.09.2011 |  | Barbados | | Trinidad and Tobago |  | 0:2 (0:1) |
| Bridgetown |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
 | 02.09.2011 |  | Trinidad and Tobago | | Bermuda |  | 1:0 (1:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
 | 12.08.2009 |  | Trinidad and Tobago | | El Salvador |  | 1:0 (1:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
 | 19.11.2008 |  | Trinidad and Tobago | | Cuba |  | 3:0 (0:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
 | 15.10.2008 |  | Trinidad and Tobago | | USA |  | 2:1 (0:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
 | 20.08.2008 |  | Cuba | | Trinidad and Tobago |  | 1:3 (0:1) |
| La Habana |
World Cup 2010, Qualifying tournament, CONCACAF, Second round |
 | 22.06.2008 |  | Bermuda | | Trinidad and Tobago |  | 0:2 (0:1) |
| Hamilton |
World Cup 2006, Qualifying tournament, intercontinental play-off, Playoff |
 | 16.11.2005 |  | Bahrain | | Trinidad and Tobago |  | 0:1 (0:0) |
| Riffa |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 12.10.2005 |  | Trinidad and Tobago | | Mexico |  | 2:1 (1:1) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 08.10.2005 |  | Panama | | Trinidad and Tobago |  | 0:1 (0:0) |
| Ciudad de Panamá |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 03.09.2005 |  | Trinidad and Tobago | | Guatemala |  | 3:2 (0:1) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 04.06.2005 |  | Trinidad and Tobago | | Panama |  | 2:0 (1:0) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
 | 17.11.2004 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 2:1 (0:0) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
 | 10.10.2004 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 5:1 (2:1) |
| San Fernando |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
 | 04.09.2004 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 1:2 (1:1) |
| Bassterre |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
 | 18.08.2004 |  | Saint Vincent and Grenadines | | Trinidad and Tobago |  | 0:2 (0:0) |
| Kingstown |
World Cup 2006, Qualifying tournament, CONCACAF, Second round |
 | 20.06.2004 |  | Trinidad and Tobago | | Dominican Republic |  | 4:0 (0:0) |
| San Fernando |
World Cup 2006, Qualifying tournament, CONCACAF, Second round |
 | 13.06.2004 |  | Dominican Republic | | Trinidad and Tobago |  | 0:2 (0:0) |
| Santo Domingo de Guzmán |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
 | 07.10.2001 |  | Honduras | | Trinidad and Tobago |  | 0:1 (0:0) |
| San Pedro Sula |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 15.11.2000 |  | Trinidad and Tobago | | Panama |  | 1:0 (1:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 03.09.2000 |  | Trinidad and Tobago | | Canada |  | 4:0 (2:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 16.08.2000 |  | Trinidad and Tobago | | Panama |  | 6:0 (3:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 23.07.2000 |  | Trinidad and Tobago | | Mexico |  | 1:0 (0:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 16.07.2000 |  | Canada | | Trinidad and Tobago |  | 0:2 (0:1) |
| Edmonton |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 3 |
 | 07.05.2000 |  | Trinidad and Tobago | | Haiti |  | 3:1 (1:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 2 |
 | 16.04.2000 |  | Dominican Republic | | Trinidad and Tobago |  | 0:1 (0:0) |
| Santo Domingo de Guzmán |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 2 |
 | 02.04.2000 |  | Trinidad and Tobago | | Dominican Republic |  | 3:0 (0:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
 | 04.03.2000 |  | Trinidad and Tobago | | Netherlands Antilles |  | 5:0 (2:0) |
| Port of Spain |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Third Round |
 | 23.06.1996 |  | Trinidad and Tobago | | Dominican Republic |  | 8:0 (6:0) |
| Port of Spain |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Third Round |
 | 15.06.1996 |  | Dominican Republic | | Trinidad and Tobago |  | 1:4 (0:2) |
| Santo Domingo de Guzmán |
World Cup 1994, Qualifying tournament, CONCACAF, Second preliminary round |
 | 31.05.1992 |  | Trinidad and Tobago | | Barbados |  | 3:0 (0:0) |
| Port of Spain |
World Cup 1994, Qualifying tournament, CONCACAF, Second preliminary round |
 | 19.04.1992 |  | Barbados | | Trinidad and Tobago |  | 1:2 (0:1) |
| Bridgetown |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
 | 25.11.1968 |  | Haiti | | Trinidad and Tobago |  | 2:4 (1:2) |
| Port-au-Prince |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
 | 07.02.1965 |  | Trinidad and Tobago | | Dutch Guiana |  | 4:1 (3:1) |
| Port of Spain |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Second Round |
 | |  | Trinidad and Tobago | | Bermuda |  | +:- |
| |