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 | | +:- |
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