Caribbean Championship 2014, Final tournament, Group A |
 | 15.11.2014 |  | Cuba | – | Trinidad and Tobago |  | 0:0 |
| Montego Bay |
Caribbean Championship 2014, Final tournament, Group A |
| 11.11.2014 | | Cuba | – | French Guiana |  | 1:1 (0:0) |
| Montego Bay |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
| 16.11.2012 |  | Saint Vincent and Grenadines | – | Cuba | | 1:1 (1:0) |
| Bacolet |
Caribbean Championship 2010, Final tournament, Group H |
| 30.11.2010 | | Cuba | – | Grenada |  | 0:0 |
| Fort-de-France |
Caribbean Championship 2010, Qualifying tournament, Second round, group G |
| 14.11.2010 |  | Antigua and Barbuda | – | Cuba | | 0:0 |
| St. John's |
Caribbean Championship 2010, Qualifying tournament, Second round, group G |
| 12.11.2010 |  | Suriname | – | Cuba | | 3:3 (1:1) |
| St. John's |
Caribbean Championship 2008, Final tournament, 3rd place match |
| 14.12.2008 | | Cuba | – | Guadeloupe |  | 0:0,
pen. 4:5 |
| Kingston |
Caribbean Championship 2008, Final tournament, Semifinal |
| 11.12.2008 | | Cuba | – | Grenada | | 2:2 aet
(2:1, 2:2),
pen. 5:6 |
| Kingston |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
| 25.10.2008 | | Cuba | – | Barbados |  | 1:1 (0:0) |
| La Habana |
Caribbean Cup 2007, Final tournament, Bobby Sookram Group |
| 18.01.2007 | | Cuba | – | Guyana |  | 0:0 |
| San Fernando |
Caribbean Cup 2007, Qualifying tournament, Second round, group I |
| 12.11.2006 |  | Martinique | – | Cuba | | 0:0 |
| Fort-de-France |
Caribbean Cup 2005, Qualifying tournament, Third round |
| 16.01.2005 | | Cuba | – | Haiti |  | 1:1 aet
(0:0, 0:1) |
| La Habana |
Caribbean Cup 2001, Final tournament, Group 2 |
| 20.05.2001 | | Cuba | – | Haiti | | 0:0 |
| Malabar |
Caribbean Cup 2001, Final tournament, Group 2 |
| 18.05.2001 | | Cuba | – | Saint Kitts and Nevis |  | 1:1 (0:1) |
| Tunapuna |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 06.05.1998 |  | Cayman Islands | – | Cuba | | 2:2 |
| |
Caribbean Cup 1996, Final tournament, Group B |
| 29.05.1996 | | Haiti | – | Cuba | | 0:0 |
| Arima |
Caribbean Cup 1992, Final tournament, 3rd place match |
| 27.06.1992 | | Martinique | – | Cuba | | 1:1 aet
(1:1),
pen. 5:3 |
| Port of Spain |
Caribbean Cup 1992, Final tournament, Group B |
| 17.06.1992 |  | Jamaica | – | Cuba | | 0:0 |
| |
