World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
 | 10.06.2025 |  | Costa Rica | – | Trinidad and Tobago |  | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 06.06.2025 | | Trinidad and Tobago | – | Saint Kitts and Nevis |  | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 08.06.2024 |  | Bahamas | – | Trinidad and Tobago | | |
| Saint Kitts and Nevis, Bassterre SKNFA Technical Centre |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 05.06.2024 | | Trinidad and Tobago | – | Grenada |  | |
| Port of Spain |
World Cup 2022, Qualifying tournament, CONCACAF, Group F |
| 05.06.2021 | | Bahamas | – | Trinidad and Tobago | | 0:0 |
| Nassau |
World Cup 2022, Qualifying tournament, CONCACAF, Group F |
| 28.03.2021 |  | Puerto Rico | – | Trinidad and Tobago | | 1:1 (0:0) |
| Mayagüez |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
| 02.09.2016 | | Trinidad and Tobago | – | Guatemala |  | 2:2 (1:1) |
| Port of Spain |
World Cup 2018, Qualifying tournament, CONCACAF, Fourth Round, Group C |
| 17.11.2015 | | Trinidad and Tobago | – | USA |  | 0:0 |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 14.10.2009 | | Trinidad and Tobago | – | Mexico |  | 2:2 (1:0) |
| Macoya |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 28.03.2009 | | Trinidad and Tobago | – | Honduras |  | 1:1 (0:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
| 11.02.2009 |  | El Salvador | – | Trinidad and Tobago | | 2:2 (0:2) |
| San Salvador |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
| 11.10.2008 | | Guatemala | – | Trinidad and Tobago | | 0:0 |
| Ciudad de Guatemala |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
| 06.09.2008 | | Trinidad and Tobago | – | Guatemala | | 1:1 (0:0) |
| Port of Spain |
World Cup 2006, Final tournament, Group B |
| 10.06.2006 | | Trinidad and Tobago | – | Sweden |  | 0:0 |
| Dortmund |
World Cup 2006, Qualifying tournament, intercontinental play-off, Playoff |
| 12.11.2005 | | Trinidad and Tobago | – | Bahrain |  | 1:1 (0:0) |
| Port of Spain |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
| 30.03.2005 | | Trinidad and Tobago | – | Costa Rica | | 0:0 |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 11.11.2001 | | Trinidad and Tobago | – | USA | | 0:0 |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 25.04.2001 | | Trinidad and Tobago | – | Mexico | | 1:1 (1:0) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 3 |
| 19.05.2000 |  | Haiti | – | Trinidad and Tobago | | 1:1 (0:1) |
| Port-au-Prince |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
| 18.03.2000 |  | Netherlands Antilles | – | Trinidad and Tobago | | 1:1 (0:1) |
| Willemstad |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
| 06.10.1996 | | Trinidad and Tobago | – | Guatemala | | 1:1 (1:1) |
| Port of Spain |
World Cup 1994, Qualifying tournament, CONCACAF, First Round |
| 18.08.1992 |  | Jamaica | – | Trinidad and Tobago | | 1:1 (1:1) |
| Kingston |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 20.11.1968 | | Guatemala | – | Trinidad and Tobago | | 0:0 |
| Ciudad de Guatemala |
