Caribbean Championship 2017, Qualifying tournament, First Round, Group 4 |
 | 29.03.2016 |  | Dominican Republic | | Barbados |  | 2:0 (0:0) |
| Santo Domingo de Guzmán |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 4 |
 | 23.03.2016 |  | Barbados | | Curaçao |  | 1:0 (0:0) |
| Cave Hill |
Caribbean Championship 2014, Qualifying tournament, Second round, group 8 |
 | 12.10.2014 |  | Barbados | | French Guiana |  | 0:2 (0:1) |
| Port-au-Prince |
Caribbean Championship 2014, Qualifying tournament, Second round, group 8 |
 | 10.10.2014 |  | Haiti | | Barbados |  | 4:2 (3:2) |
| Port-au-Prince |
Caribbean Championship 2014, Qualifying tournament, Second round, group 8 |
 | 08.10.2014 |  | Saint Kitts and Nevis | | Barbados |  | 2:3 (1:3) |
| Port-au-Prince |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 3 |
 | 07.09.2014 |  | Bonaire | | Barbados |  | 1:4 (0:0) |
| Fort-de-France |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 3 |
 | 05.09.2014 |  | Martinique | | Barbados |  | 3:2 (0:2) |
| Fort-de-France |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 3 |
 | 03.09.2014 |  | Barbados | | Suriname |  | 1:1 (0:0) |
| Fort-de-France |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 4 |
 | 27.09.2012 |  | Barbados | | Aruba |  | 2:1 (1:1) |
| Bridgetown |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 4 |
 | 25.09.2012 |  | Barbados | | Dominican Republic |  | 0:1 (0:0) |
| Bridgetown |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 4 |
 | 23.09.2012 |  | Barbados | | Dominica |  | 1:0 (1:0) |
| Bridgetown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
 | 10.10.2010 |  | Saint Vincent and Grenadines | | Barbados |  | 0:0 |
| Kingstown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
 | 08.10.2010 |  | Montserrat | | Barbados |  | 0:5 (0:2) |
| Kingstown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
 | 06.10.2010 |  | Barbados | | Saint Kitts and Nevis |  | 1:1 (1:0) |
| Kingstown |
Caribbean Championship 2008, Final tournament, Group A |
 | 07.12.2008 |  | Grenada | | Barbados |  | 4:2 (3:0) |
| Trelawny |
Caribbean Championship 2008, Final tournament, Group A |
 | 05.12.2008 |  | Barbados | | Trinidad and Tobago |  | 1:2 (1:1) |
| Montego Bay |
Caribbean Championship 2008, Final tournament, Group A |
 | 03.12.2008 |  | Jamaica | | Barbados |  | 2:1 (0:1) |
| Kingston |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
 | 27.10.2008 |  | Netherlands Antilles | | Barbados |  | 1:2 (1:2) |
| La Habana |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
 | 25.10.2008 |  | Cuba | | Barbados |  | 1:1 (0:0) |
| La Habana |
Caribbean Championship 2008, Qualifying tournament, Second round, group G |
 | 23.10.2008 |  | Barbados | | Suriname |  | 3:2 (0:2) |
| La Habana |
Caribbean Championship 2008, Qualifying tournament, First Round, Group D |
 | 28.09.2008 |  | Saint Kitts and Nevis | | Barbados |  | 1:3 (1:2) |
| Bassterre |
Caribbean Championship 2008, Qualifying tournament, First Round, Group D |
 | 26.09.2008 |  | British Virgin Islands | | Barbados |  | 1:2 (1:1) |
| Bassterre |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
 | 17.01.2007 |  | Barbados | | Martinique |  | 2:3 (2:3) |
| Port of Spain |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
 | 15.01.2007 |  | Barbados | | Haiti |  | 0:2 (0:0) |
| Port of Spain |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
 | 12.01.2007 |  | Trinidad and Tobago | | Barbados |  | 1:1 (1:0) |
| Port of Spain |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
 | 23.11.2006 |  | Barbados | | Bermuda |  | 1:1 (1:1) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
 | 21.11.2006 |  | Barbados | | Saint Vincent and Grenadines |  | 3:0 (2:0) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, Second round, group G |
 | 19.11.2006 |  | Barbados | | Bahamas |  | 2:1 (2:0) |
| Bridgetown |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
 | 24.09.2006 |  | Barbados | | Anguilla |  | 7:1 (3:0) |
| St. John's |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
 | 22.09.2006 |  | Antigua and Barbuda | | Barbados |  | 1:3 (1:1) |
| St. John's |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
 | 20.09.2006 |  | Barbados | | Saint Kitts and Nevis |  | 1:1 (1:0) |
| St. John's |
Caribbean Cup 2005, Final tournament, Final Round |
 | 24.02.2005 |  | Barbados | | Trinidad and Tobago |  | 2:3 (1:2) |
| 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 |  | Barbados | | Cuba |  | 0:3 (0:1) |
| Bridgetown |
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 |
 | 17.05.2001 |  | Barbados | | Martinique |  | 1:3 (1:1) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Group 1 |
 | 15.05.2001 |  | Trinidad and Tobago | | Barbados |  | 5:0 (2:0) |
| Malabar |
Caribbean Cup 2001, Qualifying tournament, Group 5 |
 | 08.04.2001 |  | Barbados | | Aruba |  | 5:2 (4:1) |
| Paramaribo |
Caribbean Cup 2001, Qualifying tournament, Group 5 |
 | 06.04.2001 |  | Suriname | | Barbados |  | 2:2 (1:1) |
| Paramaribo |
Caribbean Cup 2001, Qualifying tournament, Group 5 |
 | 04.04.2001 |  | Barbados | | Grenada |  | 2:1 (1:0) |
| Paramaribo |
Caribbean Cup 1999, Qualifying tournament, Group 2 |
 | 14.03.1999 |  | Guadeloupe | | Barbados |  | 1:0 |
| Pointe-à-Pitre |
Caribbean Cup 1999, Qualifying tournament, Group 2 |
 | 12.03.1999 |  | Barbados | | Dominica |  | 3:1 |
| Pointe-à-Pitre |
Caribbean Cup 1999, Qualifying tournament, Group 2 |
 | 10.03.1999 |  | Barbados | | Antigua and Barbuda |  | 2:0 |
| Pointe-à-Pitre |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group B |
 | 06.03.1999 |  | Barbados | | Guyana |  | 2:0 (2:0) |
| Bridgetown |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group B |
 | 28.02.1999 |  | Guyana | | Barbados |  | 2:2 (2:2) |
| Georgetown |
Caribbean Cup 1998, Qualifying tournament, Group 2 |
 | 22.03.1998 |  | Barbados | | Saint Vincent and Grenadines |  | 4:3 |
| Castries |
Caribbean Cup 1998, Qualifying tournament, Group 2 |
 | 20.03.1998 |  | Barbados | | Martinique |  | 1:4 |
| Castries |
Caribbean Cup 1998, Qualifying tournament, Group 2 |
 | 18.03.1998 |  | Saint Lucia | | Barbados |  | 2:1 |
| Castries |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
 | 06.04.1997 |  | Guyana | | Barbados |  | 0:2 |
| Port of Spain |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
 | 04.04.1997 |  | Trinidad and Tobago | | Barbados |  | 0:1 (0:1) |
| Port of Spain |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
 | 02.04.1997 |  | Barbados | | Grenada |  | 1:1 |
| Port of Spain |
Caribbean Cup 1996, Qualifying tournament, Group 6 |
 | 28.04.1996 |  | Barbados | | Jamaica |  | 2:0 aet (2:0), pen. 3:4 |
| |
Caribbean Cup 1996, Qualifying tournament, Group 6 |
 | 24.04.1996 |  | Jamaica | | Barbados |  | 2:0 |
| |
Caribbean Cup 1995, Qualifying tournament, Group 3, Round 2 |
 | 07.05.1995 |  | Saint Lucia | | Barbados |  | 2:1 |
| Vieux Fort |
Caribbean Cup 1995, Qualifying tournament, Group 3, Round 2 |
 | 30.04.1995 |  | Barbados | | Saint Lucia |  | 1:1 |
| Bridgetown |
Caribbean Cup 1995, Qualifying tournament, Group 3, Round 1 |
 | 02.04.1995 |  | Guyana | | Barbados |  | 0:4 |
| Georgetown |
Caribbean Cup 1995, Qualifying tournament, Group 3, Round 1 |
 | 26.03.1995 |  | Barbados | | Guyana |  | 3:0 |
| Bridgetown |
Caribbean Cup 1994, Final tournament, Group A |
 | 11.04.1994 |  | Guadeloupe | | Barbados |  | 2:2 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
 | 09.04.1994 |  | Trinidad and Tobago | | Barbados |  | 2:0 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
 | 07.04.1994 |  | Barbados | | Dominica |  | 1:1 |
| Port of Spain |
Caribbean Cup 1994, Qualifying tournament, Group 1 |
 | 27.01.1994 |  | Barbados | | Grenada |  | 4:2 aet (2:0, 2:2) |
| Bridgetown |
Caribbean Cup 1994, Qualifying tournament, Group 1 |
 | 23.01.1994 |  | Barbados | | Puerto Rico |  | 0:1 |
| Bridgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 14.03.1993 |  | Guyana | | Barbados |  | 0:3 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 12.03.1993 |  | Cayman Islands | | Barbados |  | 1:6 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 11.03.1993 |  | Puerto Rico | | Barbados |  | 1:0 |
| Georgetown |
Caribbean Cup 1992, Qualifying tournament, Group 1 |
 | 29.03.1992 |  | Barbados | | Saint Vincent and Grenadines |  | 2:3 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 1 |
 | 27.03.1992 |  | Barbados | | Netherlands Antilles |  | 1:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 1 |
 | 25.03.1992 |  | Barbados | | Grenada |  | 1:1 |
| |
Caribbean Cup 1989, Final tournament, Group A |
 | 05.07.1989 |  | Barbados | | Trinidad and Tobago |  | 0:3 |
| Bridgetown |
Caribbean Cup 1989, Final tournament, Group A |
 | 03.07.1989 |  | Barbados | | Guadeloupe |  | 1:0 |
| Bridgetown |