CONCACAF Gold Cup 2023, Final tournament, Semifinal |
 | 12.07.2023 |  | Jamaica | – | Mexico |  | 0:3 (0:2) |
| Paradise |
CONCACAF Gold Cup 2021, Final tournament, Quarterfinal |
| 25.07.2021 |  | USA | – | Jamaica | | 1:0 (0:0) |
| Arlington |
CONCACAF Gold Cup 2021, Final tournament, Group C |
| 20.07.2021 |  | Costa Rica | – | Jamaica | | 1:0 (0:0) |
| Orlando |
CONCACAF Gold Cup 2019, Final tournament, Semifinal |
| 03.07.2019 | | Jamaica | – | USA | | 1:3 (0:1) |
| Nashville |
CONCACAF Gold Cup 2017, Final tournament, Final |
| 26.07.2017 | | USA | – | Jamaica | | 2:1 (1:0) |
| Santa Clara |
CONCACAF Gold Cup 2015, Final tournament, Final |
| 26.07.2015 | | Jamaica | – | Mexico | | 1:3 (0:1) |
| USA, Philadelphia |
CONCACAF Gold Cup 2011, Final tournament, Quarterfinals |
| 19.06.2011 | | Jamaica | – | USA | | 0:2 (0:0) |
| Washington |
CONCACAF Gold Cup 2009, Final tournament, Group A |
| 07.07.2009 | | Jamaica | – | Costa Rica | | 0:1 (0:0) |
| Columbus |
CONCACAF Gold Cup 2009, Final tournament, Group A |
| 03.07.2009 |  | Canada | – | Jamaica | | 1:0 (0:0) |
| Carson |
CONCACAF Gold Cup 2005, Final tournament, Quarterfinal |
| 16.07.2005 | | USA | – | Jamaica | | 3:1 (2:0) |
| Foxborough |
CONCACAF Gold Cup 2005, Final tournament, Group C |
| 13.07.2005 | | Mexico | – | Jamaica | | 1:0 (0:0) |
| Houston |
CONCACAF Gold Cup 2003, Final tournament, Quarterfinal |
| 20.07.2003 | | Mexico | – | Jamaica | | 5:0 (2:0) |
| Mexico, Ciudad de México |
CONCACAF Gold Cup 2003, Final tournament, Group B |
| 13.07.2003 | | Jamaica | – | Colombia |  | 0:1 (0:1) |
| Miami |
CONCACAF Gold Cup 2000, Final tournament, Group A |
| 14.02.2000 | | Jamaica | – | Honduras |  | 0:2 (0:0) |
| Miami |
CONCACAF Gold Cup 2000, Final tournament, Group A |
| 12.02.2000 | | Colombia | – | Jamaica | | 1:0 (1:0) |
| Miami |
CONCACAF Gold Cup 1998, Final tournament, 3rd place match |
| 15.02.1998 |  | Brazil | – | Jamaica | | 1:0 (0:0) |
| Los Angeles |
CONCACAF Gold Cup 1998, Final tournament, Semifinal |
| 12.02.1998 | | Jamaica | – | Mexico | | 0:1 aet
(0:0, 0:0) |
| Los Angeles |
CONCACAF Gold Cup 1993, Final tournament, Semifinal |
| 22.07.1993 | | Mexico | – | Jamaica | | 6:1 (4:1) |
| Mexico, Ciudad de México |
CONCACAF Gold Cup 1993, Final tournament, Group A |
| 10.07.1993 | | USA | – | Jamaica | | 1:0 (0:0) |
| Dallas |
CONCACAF Gold Cup 1991, Final tournament, Group A |
| 03.07.1991 | | Canada | – | Jamaica | | 3:2 (1:1) |
| Los Angeles |
CONCACAF Gold Cup 1991, Final tournament, Group A |
| 30.06.1991 | | Honduras | – | Jamaica | | 5:0 (2:0) |
| Los Angeles |
CONCACAF Gold Cup 1991, Final tournament, Group A |
| 28.06.1991 | | Mexico | – | Jamaica | | 4:1 (2:1) |
| Los Angeles |
CONCACAF Championship 1989, Qualifying tournament, Second round |
| 13.08.1988 | | USA | – | Jamaica | | 5:1 (1:0) |
| Saint Louis |
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 |
CONCACAF Championship 1971, Qualifying tournament, Caribbean Zone |
| 01.10.1971 | | Jamaica | – | Cuba | | 0:1 |
| Kingston |
CONCACAF Championship 1969, Final tournament, Final Round |
| 08.12.1969 | | Costa Rica | – | Jamaica | | 3:0 |
| San José |
CONCACAF Championship 1969, Final tournament, Final Round |
| 03.12.1969 |  | Trinidad and Tobago | – | Jamaica | | 3:2 |
| San José |
CONCACAF Championship 1969, Final tournament, Final Round |
| 01.12.1969 |  | Netherlands Antilles | – | Jamaica | | 2:1 |
| San José |
CONCACAF Championship 1969, Final tournament, Final Round |
| 28.11.1969 | | Mexico | – | Jamaica | | 2:0 |
| San José |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 21.01.1967 | | Jamaica | – | Haiti |  | 0:1 |
| Kingston |
CONCACAF Championship 1963, Final tournament, Group 2 |
| 30.03.1963 | | Netherlands Antilles | – | Jamaica | | 2:1 |
| Santa Ana |
CONCACAF Championship 1963, Final tournament, Group 2 |
| 28.03.1963 | | Mexico | – | Jamaica | | 8:0 (4:0) |
| Santa Ana |
CONCACAF Championship 1963, Final tournament, Group 2 |
| 24.03.1963 | | Costa Rica | – | Jamaica | | 6:0 |
| Santa Ana |
CONCACAF Championship 1985, Qualifying tournament, First Round |
| | | Canada | – | Jamaica | | +:- |
| |
CONCACAF Championship 1973, Qualifying tournament, Caribbean Zone, group 4 |
| | | Netherlands Antilles | – | Jamaica | | +:- |
| |
