CONCACAF Gold Cup 2025, Qualifying tournament, Qualifying Round |
 | 25.03.2025 |  | Trinidad and Tobago | – | Cuba |  | 4:0 (2:0) |
| Couva |
CONCACAF Gold Cup 2025, Qualifying tournament, Qualifying Round |
| 21.03.2025 | | Cuba | – | Trinidad and Tobago | | 1:2 (1:1) |
| Santiago de Cuba |
CONCACAF Nations League 2024/25, League A, Group B |
| 14.10.2024 | | Trinidad and Tobago | – | Cuba | | 3:1 (2:0) |
| Bacolet |
CONCACAF Nations League 2024/25, League A, Group B |
| 10.10.2024 | | Cuba | – | Trinidad and Tobago | | 2:2 (0:1) |
| Santiago de Cuba |
CONCACAF Gold Cup 2015, Final tournament, Group C |
| 12.07.2015 | | Trinidad and Tobago | – | Cuba | | 2:0 (2:0) |
| USA, Glendale |
Caribbean Championship 2014, Final tournament, Group A |
| 15.11.2014 | | Cuba | – | Trinidad and Tobago | | 0:0 |
| Montego Bay |
Caribbean Championship 2012, Final tournament, Final |
| 16.12.2012 | | Cuba | – | Trinidad and Tobago | | 1:0 aet
(0:0) |
| St. John's |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
| 18.11.2012 | | Trinidad and Tobago | – | Cuba | | 1:0 (0:0) |
| Bacolet |
Caribbean Championship 2010, Final tournament, Group H |
| 26.11.2010 | | Trinidad and Tobago | – | Cuba | | 0:2 (0:1) |
| Fort-de-France |
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 |
| 20.08.2008 | | Cuba | – | Trinidad and Tobago | | 1:3 (0:1) |
| La Habana |
Caribbean Cup 2007, Final tournament, Semifinal |
| 20.01.2007 | | Trinidad and Tobago | – | Cuba | | 3:1 (1:0) |
| Port of Spain |
Caribbean Cup 2005, Final tournament, Final Round |
| 22.02.2005 | | Trinidad and Tobago | – | Cuba | | 1:2 (1:1) |
| Bridgetown |
Friendly internationals 2003 |
| 19.11.2003 | | Trinidad and Tobago | – | Cuba | | 2:1 (2:0) * |
| |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, Final Round, Group B |
| 30.03.2003 | | Trinidad and Tobago | – | Cuba | | 1:3 (1:1) |
| San Fernando |
Caribbean Cup 2001, Final tournament, Semifinal |
| 22.05.2001 | | Trinidad and Tobago | – | Cuba | | 2:0 (2:0) |
| Port of Spain |
Friendly internationals 2000 |
| 04.07.2000 | | Trinidad and Tobago | – | Cuba | | 4:1 (1:1) |
| |
Caribbean Cup 1999, Final tournament, Final |
| 13.06.1999 | | Trinidad and Tobago | – | Cuba | | 2:1 aet
(0:0, 1:1) |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Final |
| 07.06.1996 | | Trinidad and Tobago | – | Cuba | | 2:0 |
| Port of Spain |
Caribbean Cup 1995, Final tournament, Group B |
| 19.07.1995 | | Trinidad and Tobago | – | Cuba | | 2:0 (1:0) |
| Kingston |
Caribbean Cup 1992, Final tournament, Semifinal |
| 24.06.1992 | | Trinidad and Tobago | – | Cuba | | 1:0 |
| |
Olympic Games 1984, Qualifying tournament, CONCACAF, Second round |
| | | Cuba | – | Trinidad and Tobago | | 2:0 |
| |
Olympic Games 1984, Qualifying tournament, CONCACAF, Second round |
| | | Cuba | – | Trinidad and Tobago | | 1:0 * |
| |
Olympic Games 1984, Qualifying tournament, CONCACAF, Second round |
| | | Trinidad and Tobago | – | Cuba | | 2:0 |
| |
Central American and Caribbean Games 1974, Final |
| 12.03.1974 | | Cuba | – | Trinidad and Tobago | | 1:1,
pen. 3:0 |
| Santo Domingo de Guzmán |
Central American and Caribbean Games 1974, Group A |
| 04.03.1974 | | Cuba | – | Trinidad and Tobago | | 1:0 |
| Santo Domingo de Guzmán |
CONCACAF Championship 1971, Final tournament, Final Round |
| 20.11.1971 | | Trinidad and Tobago | – | Cuba | | 2:2 |
| Port of Spain |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 21.01.1967 | | Trinidad and Tobago | – | Cuba | | 2:1 |
| Kingston |
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
