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 |
