CONCACAF Gold Cup 2025, Qualifying tournament, First Round |
 | 21.03.2025 |  | Saint Vincent and Grenadines | – | Jamaica |  | 1:1 (0:0) |
| Kingstown |
CONCACAF Gold Cup 2023, Final tournament, Group A |
| 24.06.2023 |  | USA | – | Jamaica | | 1:1 (0:1) |
| Chicago |
CONCACAF Gold Cup 2019, Final tournament, Group C |
| 25.06.2019 | | Jamaica | – | Curaçao |  | 1:1 (1:0) |
| Los Angeles |
CONCACAF Gold Cup 2019, Final tournament, Group C |
| 21.06.2019 |  | El Salvador | – | Jamaica | | 0:0 |
| Houston |
CONCACAF Gold Cup 2017, Final tournament, Group C |
| 16.07.2017 | | Jamaica | – | El Salvador | | 1:1 (0:1) |
| San Antonio |
CONCACAF Gold Cup 2017, Final tournament, Group C |
| 13.07.2017 |  | Mexico | – | Jamaica | | 0:0 |
| Denver |
CONCACAF Gold Cup 2015, Final tournament, Group B |
| 08.07.2015 |  | Costa Rica | – | Jamaica | | 2:2 (2:1) |
| USA, Carson |
CONCACAF Gold Cup 2005, Final tournament, Group C |
| 10.07.2005 | | Jamaica | – | South Africa |  | 3:3 (2:2) |
| Los Angeles |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, Final Round, Group A |
| 28.03.2003 | | Jamaica | – | Martinique |  | 2:2 (0:1) |
| Kingston |
CONCACAF Gold Cup 2003, Qualifying tournament, Caribbean Zone, First Round, Group C |
| 09.11.2002 | | Jamaica | – | Barbados |  | 1:1 (0:0) |
| Saint George's |
CONCACAF Gold Cup 1998, Final tournament, Group A |
| 03.02.1998 |  | Brazil | – | Jamaica | | 0:0 |
| Miami |
CONCACAF Gold Cup 1993, Final tournament, 3rd place match |
| 25.07.1993 | | Costa Rica | – | Jamaica | | 1:1 aet
(1:0, 1:1) |
| Mexico, Ciudad de México |
CONCACAF Gold Cup 1993, Final tournament, Group A |
| 17.07.1993 | | Jamaica | – | Panama |  | 1:1 (0:0) |
| Dallas |
CONCACAF Championship 1989, Qualifying tournament, Second round |
| 24.07.1988 | | Jamaica | – | USA | | 0:0 |
| Kingston |
CONCACAF Championship 1971, Qualifying tournament, Caribbean Zone |
| 04.10.1971 |  | Cuba | – | Jamaica | | 0:0 |
| La Habana |
CONCACAF Championship 1969, Final tournament, Final Round |
| 04.12.1969 |  | Guatemala | – | Jamaica | | 0:0 |
| San José |
CONCACAF Championship 1969, Qualifying tournament, Qualifying round |
| 04.11.1969 | | Jamaica | – | Panama | | 1:1 |
| Kingston |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 18.01.1967 | | Jamaica | – | Trinidad and Tobago |  | 1:1 |
| Kingston |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 11.01.1967 | | Jamaica | – | Netherlands Antilles |  | 1:1 |
| Kingston |
