World Cup 2022, Qualifying tournament, CONCACAF, Group C |
 | 08.06.2021 |  | Saint Vincent and Grenadines | – | Cuba |  | 0:1 (0:0) |
| Grenada, Saint George's |
World Cup 2022, Qualifying tournament, CONCACAF, Group C |
| 02.06.2021 | | Cuba | – | British Virgin Islands |  | 5:0 (1:0) |
| Guatemala, Ciudad de Guatemala |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 1 |
| 15.10.2008 | | Cuba | – | Guatemala |  | 2:1 (1:0) |
| La Habana |
World Cup 2010, Qualifying tournament, CONCACAF, Second round |
| 22.06.2008 | | Cuba | – | Antigua and Barbuda |  | 4:0 (2:0) |
| La Habana |
World Cup 2010, Qualifying tournament, CONCACAF, Second round |
| 17.06.2008 | | Antigua and Barbuda | – | Cuba | | 3:4 (2:2) |
| St. John's |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 27.03.2004 | | Cuba | – | Cayman Islands |  | 3:0 (1:0) |
| La Habana |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 22.02.2004 | | Cayman Islands | – | Cuba | | 1:2 (0:0) |
| George Town |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 2 |
| 02.04.2000 | | Cuba | – | Suriname |  | 1:0 (1:0) |
| La Habana |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 1 |
| 05.03.2000 | | Cuba | – | Cayman Islands | | 4:0 (1:0) |
| La Habana |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 2 |
| 22.09.1996 |  | Panama | – | Cuba | | 1:3 (0:1) |
| Ciudad de Panamá |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Third Round |
| 10.06.1996 | | Cuba | – | Haiti |  | 6:1 (2:0) |
| Trinidad and Tobago, Port of Spain |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Second Round |
| 14.05.1996 | | Cayman Islands | – | Cuba | | 0:5 (0:1) |
| George Town |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Second Round |
| 12.05.1996 | | Cayman Islands | – | Cuba | | 0:1 (0:1) |
| George Town |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 08.02.1965 | | Cuba | – | Jamaica |  | 2:1 (2:1) |
| La Habana |
World Cup 1938, Final tournament, 1/8 finals |
| 09.06.1938 | | Cuba | – | Romania |  | 2:1 (0:1) * |
| Toulouse |
World Cup 1934, Qualifying tournament, Group 11, Round 1 |
| 04.02.1934 | | Haiti | – | Cuba | | 0:6 |
| Port-au-Prince Parc Leconte |
World Cup 1934, Qualifying tournament, Group 11, Round 1 |
| 28.01.1934 | | Haiti | – | Cuba | | 1:3 (0:1) |
| Port-au-Prince Parc Leconte |
World Cup 1938, Qualifying tournament, Group 11, Round 2 |
| | | Cuba | – | USA |  | +:- |
| |
