CONCACAF Nations League 2024/25, League A, Group B |
 | 06.09.2024 |  | Jamaica | – | Cuba |  | 0:0 |
| Kingston |
Friendly internationals 2015 |
| 30.03.2015 | | Jamaica | – | Cuba | | 3:0 (3:0) |
| Montego Bay |
Caribbean Championship 2012, Final tournament, Group B |
| 12.12.2012 | | Jamaica | – | Cuba | | 0:1 (0:0) |
| St. John's |
Friendly internationals 2012 |
| 24.02.2012 | | Jamaica | – | Cuba | | 3:0 (2:0) |
| Montego Bay |
Friendly internationals 2012 |
| 22.02.2012 | | Jamaica | – | Cuba | | 1:0 (0:0) |
| Kingston |
Caribbean Cup 2005, Final tournament, Final Round |
| 24.02.2005 | | Cuba | – | Jamaica | | 0:1 (0:0) |
| Bridgetown |
Friendly internationals 2003 |
| 06.07.2003 | | Jamaica | – | Cuba | | 1:2 (0:2) |
| |
Friendly internationals 2003 |
| 13.03.2003 | | Cuba | – | Jamaica | | 1:0 (1:0) |
| |
Friendly internationals 2003 |
| 11.03.2003 | | Cuba | – | Jamaica | | 0:0 |
| |
Friendly internationals 2001 |
| 20.07.2001 | | Cuba | – | Jamaica | | 0:0 |
| |
Friendly internationals 2001 |
| 10.06.2001 | | Jamaica | – | Cuba | | 4:1 (3:0) |
| |
Friendly internationals 2000 |
| 02.07.2000 | | Jamaica | – | Cuba | | 1:1 (0:1) |
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Caribbean Cup 1999, Final tournament, Semifinal |
| 10.06.1999 | | Jamaica | – | Cuba | | 0:2 (0:0) |
| Port of Spain |
Friendly internationals 1996 |
| 14.01.1996 | | Jamaica | – | Cuba | | 1:1 |
| |
Caribbean Cup 1995, Final tournament, Group B |
| 21.07.1995 | | Jamaica | – | Cuba | | 1:2 (1:1) |
| Montego Bay |
Friendly internationals 1995 |
| 12.03.1995 | | Jamaica | – | Cuba | | 0:0 |
| |
Caribbean Cup 1992, Final tournament, Group B |
| 17.06.1992 | | Jamaica | – | Cuba | | 0:0 |
| |
Friendly internationals 1987 |
| 29.04.1987 | | Jamaica | – | Cuba | | 2:0 |
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Olympic Games 1984, Qualifying tournament, CONCACAF, First Preliminary Round |
| | | Cuba | – | Jamaica | | 4:1 |
| |
Olympic Games 1984, Qualifying tournament, CONCACAF, First Preliminary Round |
| | | Jamaica | – | Cuba | | 0:1 |
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Olympic Games 1980, Qualifying tournament, CONCACAF, First Round |
| | | Cuba | – | Jamaica | | 2:0 |
| |
Olympic Games 1980, Qualifying tournament, CONCACAF, First Round |
| | | Jamaica | – | Cuba | | 0:3 |
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CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup B, Round 1 |
| 29.08.1976 | | Cuba | – | Jamaica | | 2:0 (1:0) |
| La Habana |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup B, Round 1 |
| 15.08.1976 | | Jamaica | – | Cuba | | 1:3 (0:1) |
| Kingston |
Olympic Games 1976, Qualifying tournament, CONCACAF, First Round |
| | | Cuba | – | Jamaica | | 1:0 |
| |
Olympic Games 1976, Qualifying tournament, CONCACAF, First Round |
| | | Cuba | – | Jamaica | | 4:1 * |
| |
Olympic Games 1976, Qualifying tournament, CONCACAF, First Round |
| | | Jamaica | – | Cuba | | 1:0 |
| |
CONCACAF Championship 1971, Qualifying tournament, Caribbean Zone |
| 04.10.1971 | | Cuba | – | Jamaica | | 0:0 |
| La Habana |
CONCACAF Championship 1971, Qualifying tournament, Caribbean Zone |
| 01.10.1971 | | Jamaica | – | Cuba | | 0:1 |
| Kingston |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 14.01.1967 | | Jamaica | – | Cuba | | 2:1 |
| Kingston |
Central American and Caribbean Games 1966, Final Round |
| 12.06.1966 | | Cuba | – | Jamaica | | 7:0 |
| San Juan |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 08.02.1965 | | Cuba | – | Jamaica | | 2:1 (2:1) |
| La Habana |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 16.01.1965 | | Jamaica | – | Cuba | | 2:0 (1:0) |
| Kingston |
Central American and Caribbean Games 1962, Final Round |
| 24.08.1962 | | Jamaica | – | Cuba | | 6:1 (2:0) |
| Kingston |
Central American and Caribbean Games 1930, Group A |
| 16.03.1930 | | Cuba | – | Jamaica | | 3:1 |
| La Habana |
