Caribbean Championship 2017, Qualifying tournament, Third round, group 1 |
 | 13.11.2016 |  | Jamaica | – | Suriname |  | 1:0 (1:0) * |
| Kingston |
Caribbean Championship 2017, Qualifying tournament, Third round, group 1 |
| 11.10.2016 |  | Guyana | – | Jamaica | | 2:4 aet
(2:0, 2:2) |
| Providence |
Caribbean Championship 2014, Final tournament, Group B |
| 16.11.2014 | | Jamaica | – | Haiti |  | 2:0 (2:0) |
| Montego Bay |
Caribbean Championship 2014, Final tournament, Group B |
| 14.11.2014 | | Jamaica | – | Antigua and Barbuda |  | 3:0 (2:0) |
| Montego Bay |
Caribbean Championship 2010, Final tournament, Semifinal |
| 03.12.2010 | | Jamaica | – | Grenada |  | 2:1 aet
(1:1, 1:1) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group I |
| 01.12.2010 | | Guyana | – | Jamaica | | 0:4 (0:1) |
| Rivière-Pilote |
Caribbean Championship 2010, Final tournament, Group I |
| 29.11.2010 |  | Guadeloupe | – | Jamaica | | 0:2 (0:0) |
| Rivière-Pilote |
Caribbean Championship 2010, Final tournament, Group I |
| 27.11.2010 | | Jamaica | – | Antigua and Barbuda | | 3:1 (3:0) |
| Rivière-Pilote |
Caribbean Championship 2008, Final tournament, Final |
| 14.12.2008 | | Jamaica | – | Grenada | | 2:0 (1:0) |
| Kingston |
Caribbean Championship 2008, Final tournament, Semifinal |
| 11.12.2008 | | Jamaica | – | Guadeloupe | | 2:0 (1:0) |
| Kingston |
Caribbean Championship 2008, Final tournament, Group A |
| 05.12.2008 | | Jamaica | – | Grenada | | 4:0 (2:0) |
| Montego Bay |
Caribbean Championship 2008, Final tournament, Group A |
| 03.12.2008 | | Jamaica | – | Barbados |  | 2:1 (0:1) |
| Kingston |
Caribbean Cup 2007, Qualifying tournament, First Round, Group D |
| 01.10.2006 | | Jamaica | – | Haiti | | 2:0 (2:0) |
| Kingston |
Caribbean Cup 2007, Qualifying tournament, First Round, Group D |
| 27.09.2006 | | Jamaica | – | Saint Lucia |  | 4:0 (4:0) |
| Kingston |
Caribbean Cup 2005, Final tournament, Final Round |
| 24.02.2005 |  | Cuba | – | Jamaica | | 0:1 (0:0) |
| Bridgetown |
Caribbean Cup 2005, Final tournament, Final Round |
| 22.02.2005 | | Barbados | – | Jamaica | | 0:1 (0:1) |
| Bridgetown |
Caribbean Cup 2005, Final tournament, Final Round |
| 20.02.2005 | | Jamaica | – | Trinidad and Tobago |  | 2:1 (2:1) |
| Bridgetown |
Caribbean Cup 2005, Qualifying tournament, Third round |
| 08.01.2005 | | Jamaica | – | French Guiana |  | 5:0 (1:0) |
| Kingston |
Caribbean Cup 2005, Qualifying tournament, Second round |
| 19.12.2004 | | Jamaica | – | Saint Lucia | | 2:1 (1:1) |
| Kingston |
Caribbean Cup 2005, Qualifying tournament, Group A |
| 28.11.2004 | | Jamaica | – | Haiti | | 3:1 (3:1) |
| Kingston |
Caribbean Cup 2005, Qualifying tournament, Group A |
| 26.11.2004 | | Jamaica | – | US Virgin Islands |  | 11:1 (5:0) |
| Montego Bay |
Caribbean Cup 2005, Qualifying tournament, Group A |
| 24.11.2004 | | Jamaica | – | St. Martin |  | 12:0 (9:0) |
| Kingston |
Caribbean Cup 2001, Final tournament, Group 1 |
| 19.05.2001 | | Jamaica | – | Barbados | | 2:1 (2:1) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Group 1 |
| 15.05.2001 | | Jamaica | – | Martinique |  | 1:0 (0:0) |
| Malabar |
Caribbean Cup 1999, Final tournament, Group A |
| 07.06.1999 | | Jamaica | – | Grenada | | 2:1 (0:1) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Group A |
| 05.06.1999 | | Jamaica | – | Guadeloupe | | 5:1 (1:0) |
| Port of Spain |
Caribbean Cup 1998, Final tournament, Final |
| 31.07.1998 | | Trinidad and Tobago | – | Jamaica | | 1:2 (0:2) |
| Trinidad and Tobago |
Caribbean Cup 1998, Final tournament, Semifinal |
| 29.07.1998 | | Jamaica | – | Antigua and Barbuda | | 1:0 aet
(0:0) |
| Trinidad and Tobago |
Caribbean Cup 1998, Final tournament, Group B |
| 26.07.1998 | | Jamaica | – | Haiti | | 2:1 |
| |
Caribbean Cup 1998, Final tournament, Group B |
| 24.07.1998 | | Jamaica | – | Netherlands Antilles |  | 3:2 |
| |
Caribbean Cup 1998, Final tournament, Group B |
| 22.07.1998 | | Jamaica | – | Cayman Islands |  | 4:0 |
| |
Caribbean Cup 1997, Final tournament, 3rd place match |
| 13.07.1997 | | Jamaica | – | Grenada | | 4:1 (3:1) |
| St. Kitts and Nevis, Bassterre |
Caribbean Cup 1997, Final tournament, Group A |
| 08.07.1997 | | Antigua and Barbuda | – | Jamaica | | 0:2 (0:1) |
| St. John's |
Caribbean Cup 1997, Qualifying tournament, Playoff |
| 04.05.1997 |  | Aruba | – | Jamaica | | 0:6 |
| Oranjestad |
Caribbean Cup 1997, Qualifying tournament, Group 2 |
| 23.03.1997 | | Jamaica | – | Bermuda |  | 3:2 |
| Kingston |
Caribbean Cup 1997, Qualifying tournament, Group 2 |
| 21.02.1997 | | Jamaica | – | Bermuda | | 1:0 |
| Kingston |
Caribbean Cup 1996, Final tournament, Group A |
| 26.05.1996 | | Jamaica | – | Saint Kitts and Nevis |  | 4:1 (1:0) |
| Palo Seco |
Caribbean Cup 1996, Qualifying tournament, Group 6 |
| 24.04.1996 | | Jamaica | – | Barbados | | 2:0 |
| |
Caribbean Cup 1995, Final tournament, Group B |
| 23.07.1995 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
Caribbean Cup 1995, Final tournament, Group B |
| 19.07.1995 | | Jamaica | – | Saint Lucia | | 2:1 (1:1) |
| Kingston |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 04.03.1994 | | Jamaica | – | British Virgin Islands |  | 12:0 |
| George Town |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 02.03.1994 | | Jamaica | – | Sint Maarten |  | 4:2 aet
(2:2) |
| George Town |
Caribbean Cup 1993, Final tournament, Semifinal |
| 28.05.1993 | | Jamaica | – | Trinidad and Tobago | | 3:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 25.05.1993 | | Jamaica | – | Puerto Rico |  | 1:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 23.05.1993 | | Jamaica | – | Sint Maarten | | 2:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 21.05.1993 | | Jamaica | – | Saint Kitts and Nevis | | 4:1 |
| Kingston |
Caribbean Cup 1992, Final tournament, Semifinal |
| 24.06.1992 | | Jamaica | – | Martinique | | 1:0 |
| |
Caribbean Cup 1992, Final tournament, Group B |
| 21.06.1992 | | Jamaica | – | Saint Vincent and Grenadines |  | 2:0 |
| |
Caribbean Cup 1992, Final tournament, Group B |
| 19.06.1992 | | Jamaica | – | Guadeloupe | | 1:0 |
| |
Caribbean Cup 1991, Final tournament, Final |
| 02.06.1991 | | Jamaica | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kingston |
Caribbean Cup 1991, Final tournament, Semifinal |
| 30.05.1991 | | Jamaica | – | Saint Lucia | | 2:0 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group A |
| 27.05.1991 | | Jamaica | – | Cayman Islands | | 3:2 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group A |
| 23.05.1991 | | Jamaica | – | Guyana | | 6:0 |
| Kingston |
Caribbean Cup 1997, Qualifying tournament, Playoff |
| | | Jamaica | – | Aruba | | +:- |
| |
