Caribbean Championship 2017, Qualifying tournament, First Round, Group 3 |
 | 22.03.2016 |  | Cuba | – | Bermuda |  | 2:1 (1:0) |
| La Habana |
Caribbean Championship 2014, Final tournament, Group A |
| 13.11.2014 |  | Curaçao | – | Cuba | | 2:3 (1:1) |
| 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, Final tournament, Semifinal |
| 14.12.2012 |  | Haiti | – | Cuba | | 0:1 (0:1) |
| St. John's |
Caribbean Championship 2012, Final tournament, Group B |
| 12.12.2012 |  | Jamaica | – | Cuba | | 0:1 (0:0) |
| St. John's |
Caribbean Championship 2012, Final tournament, Group B |
| 10.12.2012 | | Cuba | – | French Guiana |  | 2:1 (0:1) |
| St. John's |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
| 14.11.2012 | | Cuba | – | Suriname |  | 5:0 (2:0) |
| Bacolet |
Caribbean Championship 2010, Final tournament, 3rd place match |
| 05.12.2010 |  | Grenada | – | Cuba | | 0:1 (0:1) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group H |
| 28.11.2010 |  | Martinique | – | Cuba | | 0:1 (0:0) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group H |
| 26.11.2010 | | Trinidad and Tobago | – | Cuba | | 0:2 (0:1) |
| Fort-de-France |
Caribbean Championship 2010, Qualifying tournament, Second round, group G |
| 10.11.2010 | | Cuba | – | Dominica |  | 4:2 (4:1) |
| St. John's |
Caribbean Championship 2008, Final tournament, Group B |
| 06.12.2008 | | Cuba | – | Antigua and Barbuda |  | 3:0 (3:0) |
| Trelawny |
Caribbean Championship 2008, Final tournament, Group B |
| 04.12.2008 |  | Guadeloupe | – | Cuba | | 1:2 (1:1) |
| Montego Bay |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
| 27.10.2008 | | Cuba | – | Suriname | | 6:0 (2:0) |
| La Habana |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
| 23.10.2008 | | Cuba | – | Netherlands Antilles |  | 7:1 (4:0) |
| La Habana |
Caribbean Cup 2007, Final tournament, 3rd place match |
| 23.01.2007 | | Cuba | – | Guadeloupe | | 2:1 (1:0) |
| Port of Spain |
Caribbean Cup 2007, Final tournament, Bobby Sookram Group |
| 16.01.2007 | | Cuba | – | Saint Vincent and Grenadines |  | 3:0 (1:0) |
| San Fernando |
Caribbean Cup 2007, Qualifying tournament, Second round, group I |
| 10.11.2006 | | Cuba | – | Suriname | | 3:1 (3:0) |
| Fort-de-France |
Caribbean Cup 2007, Qualifying tournament, Second round, group I |
| 08.11.2006 | | Cuba | – | Haiti | | 2:1 (1:0) |
| Fort-de-France |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 06.09.2006 | | Cuba | – | Cayman Islands |  | 7:0 (4:0) |
| La Habana |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 04.09.2006 | | Cuba | – | Bahamas |  | 6:0 (4:0) |
| La Habana |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 02.09.2006 | | Cuba | – | Turks and Caicos Islands |  | 6:0 (3:0) |
| La Habana |
Caribbean Cup 2005, Final tournament, Final Round |
| 22.02.2005 | | Trinidad and Tobago | – | Cuba | | 1:2 (1:1) |
| Bridgetown |
Caribbean Cup 2005, Final tournament, Final Round |
| 20.02.2005 |  | Barbados | – | Cuba | | 0:3 (0:1) |
| Bridgetown |
Caribbean Cup 2005, Qualifying tournament, Third round |
| 09.01.2005 | | Haiti | – | Cuba | | 0:1 (0:0) |
| Port-au-Prince |
Caribbean Cup 2005, Qualifying tournament, Second round |
| 21.12.2004 | | Martinique | – | Cuba | | 0:2 (0:1) |
| Fort-de-France |
Caribbean Cup 2005, Qualifying tournament, Second round |
| 12.12.2004 | | Cuba | – | Martinique | | 2:0 (1:0) |
| La Habana |
Caribbean Cup 2001, Final tournament, Group 2 |
| 16.05.2001 | | Cuba | – | Suriname | | 4:3 (2:2) |
| Tunapuna |
Caribbean Cup 2001, Qualifying tournament, Group 1 |
| 08.04.2001 |  | Guyana | – | Cuba | | 0:3 (0:1) |
| Georgetown |
Caribbean Cup 2001, Qualifying tournament, Group 1 |
| 06.04.2001 | | Cuba | – | Sint Maarten |  | 1:0 (1:0) |
| Uitvlugt |
Caribbean Cup 2001, Qualifying tournament, Group 1 |
| 04.04.2001 | | Cuba | – | Dominica | | 3:1 (1:0) |
| Uitvlugt |
Caribbean Cup 1999, Final tournament, Semifinal |
| 10.06.1999 | | Jamaica | – | Cuba | | 0:2 (0:0) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Group B |
| 08.06.1999 | | Cuba | – | Saint Kitts and Nevis |  | 2:0 (1:0) |
| Macoya |
Caribbean Cup 1999, Final tournament, Group B |
| 06.06.1999 | | Cuba | – | Brazil U20 |  | 1:0 (1:0) |
| Macoya |
Caribbean Cup 1999, Final tournament, Group B |
| 04.06.1999 | | Cuba | – | Haiti | | 3:1 (2:1) |
| Macoya |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 09.05.1999 | | Bermuda | – | Cuba | | 1:2 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 07.05.1999 | | Cuba | – | Bahamas | | 7:0 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 05.05.1999 | | Cayman Islands | – | Cuba | | 1:4 (1:3) |
| Hamilton |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 08.05.1998 | | Bermuda | – | Cuba | | 1:2 |
| |
Caribbean Cup 1996, Final tournament, Semifinal |
| 02.06.1996 | | Cuba | – | Suriname | | 4:0 (1:0) |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group B |
| 27.05.1996 | | Cuba | – | Martinique | | 1:0 |
| San Fernando |
Caribbean Cup 1996, Final tournament, Group B |
| 25.05.1996 | | Cuba | – | Saint Vincent and Grenadines | | 2:0 |
| San Fernando |
Caribbean Cup 1996, Qualifying tournament, Group 4 |
| 26.04.1996 | | Cuba | – | Cayman Islands | | 4:0 |
| |
Caribbean Cup 1995, Final tournament, 3rd place match |
| 30.07.1995 | | Cayman Islands | – | Cuba | | 0:3 (0:1) |
| Cayman Islands |
Caribbean Cup 1995, Final tournament, Group B |
| 23.07.1995 | | Cuba | – | Saint Lucia |  | 2:0 (2:0) |
| Kingston |
Caribbean Cup 1995, Final tournament, Group B |
| 21.07.1995 | | Jamaica | – | Cuba | | 1:2 (1:1) |
| Montego Bay |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
| 27.05.1995 | | Cuba | – | Puerto Rico |  | 9:0 |
| La Habana |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
| 25.05.1995 |  | Dominican Republic | – | Cuba | | 0:3 |
| La Habana |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
| 23.05.1995 | | Cuba | – | Netherlands Antilles | | 3:0 |
| La Habana |
Caribbean Cup 1992, Final tournament, Group B |
| 21.06.1992 | | Cuba | – | Guadeloupe | | 2:0 |
| |
Caribbean Cup 1992, Final tournament, Group B |
| 19.06.1992 | | Cuba | – | Saint Vincent and Grenadines | | 1:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 6 |
| 09.05.1992 | | Cuba | – | Anguilla |  | 5:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 6 |
| 02.05.1992 | | Anguilla | – | Cuba | | 0:3 |
| |
