World Cup 2026, Qualifying tournament, CONCACAF, Third Round, Group B |
 | 09.09.2025 | | Jamaica | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kingston |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 10.06.2025 | | Costa Rica | – | Trinidad and Tobago | | 2:1 (2:0) |
| San José |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 06.10.2017 | | Mexico | – | Trinidad and Tobago | | 3:1 (0:0) |
| San Luis Potosí |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 05.09.2017 | | Panama | – | Trinidad and Tobago | | 3:0 (1:0) |
| Ciudad de Panamá |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 01.09.2017 | | Trinidad and Tobago | – | Honduras | | 1:2 (0:2) |
| Couva |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 13.06.2017 | | Costa Rica | – | Trinidad and Tobago | | 2:1 (2:1) |
| San José |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 08.06.2017 | | USA | – | Trinidad and Tobago | | 2:0 (0:0) |
| Commerce City |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 28.03.2017 | | Trinidad and Tobago | – | Mexico | | 0:1 (0:0) |
| Port of Spain |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 15.11.2016 | | Honduras | – | Trinidad and Tobago | | 3:1 (2:0) |
| San Pedro Sula |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
| 11.11.2016 | | Trinidad and Tobago | – | Costa Rica | | 0:2 (0:0) |
| Port of Spain |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
| 06.09.2016 | | USA | – | Trinidad and Tobago | | 4:0 (1:0) |
| Jacksonville |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
| 11.11.2011 | | Guyana | – | Trinidad and Tobago | | 2:1 (1:0) |
| Providence |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
| 07.10.2011 | | Bermuda | – | Trinidad and Tobago | | 2:1 (0:0) |
| Hamilton |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 10.10.2009 | | Costa Rica | – | Trinidad and Tobago | | 4:0 (1:0) |
| San José |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 09.09.2009 | | Trinidad and Tobago | – | USA | | 0:1 (0:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 05.09.2009 | | Honduras | – | Trinidad and Tobago | | 4:1 (2:0) |
| San Pedro Sula |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 10.06.2009 | | Mexico | – | Trinidad and Tobago | | 2:1 (1:1) |
| Ciudad de México |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 06.06.2009 | | Trinidad and Tobago | – | Costa Rica | | 2:3 (1:1) |
| Bacolet |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 01.04.2009 | | USA | – | Trinidad and Tobago | | 3:0 (1:0) |
| Nashville |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
| 10.09.2008 | | USA | – | Trinidad and Tobago | | 3:0 (2:0) |
| Bridgeview |
World Cup 2010, Qualifying tournament, CONCACAF, Second round |
| 15.06.2008 | | Trinidad and Tobago | – | Bermuda | | 1:2 (1:2) |
| Port of Spain |
World Cup 2006, Final tournament, Group B |
| 20.06.2006 | | Paraguay | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kaiserslautern |
World Cup 2006, Final tournament, Group B |
| 15.06.2006 | | England | – | Trinidad and Tobago | | 2:0 (0:0) |
| Nürnberg |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 07.09.2005 | | Costa Rica | – | Trinidad and Tobago | | 2:0 (1:0) |
| San José |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 17.08.2005 | | USA | – | Trinidad and Tobago | | 1:0 (1:0) |
| Hartford |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 08.06.2005 | | Mexico | – | Trinidad and Tobago | | 2:0 (0:0) |
| Monterrey |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 26.03.2005 | | Guatemala | – | Trinidad and Tobago | | 5:1 (3:1) |
| Ciudad de Guatemala |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 09.02.2005 | | Trinidad and Tobago | – | USA | | 1:2 (0:1) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 13.10.2004 | | Mexico | – | Trinidad and Tobago | | 3:0 (1:0) |
| Puebla de Zaragoza |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 08.09.2004 | | Trinidad and Tobago | – | Mexico | | 1:3 (1:2) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 05.09.2001 | | Mexico | – | Trinidad and Tobago | | 3:0 (2:0) |
| Ciudad de México |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 01.09.2001 | | Trinidad and Tobago | – | Costa Rica | | 0:2 (0:2) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 30.06.2001 | | Trinidad and Tobago | – | Jamaica | | 1:2 (1:1) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 20.06.2001 | | USA | – | Trinidad and Tobago | | 2:0 (2:0) |
| Foxborough |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 16.06.2001 | | Trinidad and Tobago | – | Honduras | | 2:4 (0:2) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 28.03.2001 | | Costa Rica | – | Trinidad and Tobago | | 3:0 (0:0) |
| Alajuela |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 28.02.2001 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
World Cup 2002, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 08.10.2000 | | Mexico | – | Trinidad and Tobago | | 7:0 (4:0) |
| Ciudad de México |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 21.12.1996 | | Costa Rica | – | Trinidad and Tobago | | 2:1 (2:1) |
| Cartago |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 08.12.1996 | | Guatemala | – | Trinidad and Tobago | | 2:1 (1:1) |
| USA, Los Angeles |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 24.11.1996 | | Trinidad and Tobago | – | USA | | 0:1 (0:1) |
| Port of Spain |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 10.11.1996 | | USA | – | Trinidad and Tobago | | 2:0 (0:0) |
| Richmond |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 01.09.1996 | | Trinidad and Tobago | – | Costa Rica | | 0:1 (0:0) |
| Port of Spain |
World Cup 1994, Qualifying tournament, CONCACAF, First Round |
| 05.07.1992 | | Trinidad and Tobago | – | Jamaica | | 1:2 (0:0) |
| Port of Spain |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 23.11.1968 | | Haiti | – | Trinidad and Tobago | | 4:0 (1:0) |
| Port-au-Prince |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 17.11.1968 | | Guatemala | – | Trinidad and Tobago | | 4:0 (1:0) |
| Ciudad de Guatemala |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
| 14.03.1965 | | Dutch Guiana | – | Trinidad and Tobago | | 6:1 (4:1) |
| Paramaribo |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
| 07.03.1965 | | Trinidad and Tobago | – | Costa Rica | | 0:1 (0:1) |
| Port of Spain |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
| 21.02.1965 | | Costa Rica | – | Trinidad and Tobago | | 4:0 (1:0) |
| San José |
