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 |
Superclásico
Copa Newton
Copa Lipton
Copa Rosa
Copa Félix Bogado
Copa Carlos Dittborn
Copa Ramón Castilla
Copa Rio Branco
Copa Rodrigues Alves
Taça Bernardo O'Higgins
Copa Artigas
Copa Paz del Chaco
Copa del Pacífico
