Caribbean Championship 2017, Final tournament, Final |
| 25.06.2017 | | Jamaica | | Curaçao | | 1:2 (0:1) |
| Fort-de-France |
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 |
| 08.12.2012 | | Jamaica | | French Guiana | | 1:2 (1:1) |
| St. John's |
Caribbean Cup 2007, Qualifying tournament, First Round, Group D |
| 29.09.2006 | | Jamaica | | Saint Vincent and Grenadines | | 1:2 (0:0) |
| Kingston |
Caribbean Cup 2001, Final tournament, Group 1 |
| 17.05.2001 | | Trinidad and Tobago | | Jamaica | | 2:1 (0:1) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, 3rd place match |
| 13.06.1999 | | Jamaica | | Haiti | | -:- |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Semifinal |
| 10.06.1999 | | Jamaica | | Cuba | | 0:2 (0:0) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Group A |
| 03.06.1999 | | Trinidad and Tobago | | Jamaica | | 1:0 (1:0) |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
| 28.05.1996 | | Suriname | | Jamaica | | 3:1 |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
| 24.05.1996 | | Trinidad and Tobago | | Jamaica | | 1:0 |
| Port of Spain |
Caribbean Cup 1996, Qualifying tournament, Group 6 |
| 28.04.1996 | | Barbados | | Jamaica | | 2:0 aet (2:0), pen. 3:4 |
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Caribbean Cup 1995, Final tournament, Group B |
| 21.07.1995 | | Jamaica | | Cuba | | 1:2 (1:1) |
| Montego Bay |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 06.03.1994 | | Cayman Islands | | Jamaica | | 3:2 (2:1) |
| George Town |
Caribbean Cup 1992, Final tournament, Final |
| 27.06.1992 | | Trinidad and Tobago | | Jamaica | | 3:1 (2:0) |
| Port of Spain |
Caribbean Cup 1989, Qualifying tournament, Zone C |
| ??.05.1989 | | Jamaica | | Guadeloupe | | 0:3 |
| |
Caribbean Cup 1989, Qualifying tournament, Zone C |
| 23.04.1989 | | Antigua and Barbuda | | Jamaica | | 1:0 |
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