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 |
| 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 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 |
| 23.09.2012 | | Barbados | – | Dominica |  | 1:0 (1:0) |
| Bridgetown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 08.10.2010 |  | Montserrat | – | Barbados | | 0:5 (0:2) |
| Kingstown |
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 |
| 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, 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 2001, Qualifying tournament, Group 5 |
| 08.04.2001 | | Barbados | – | Aruba | | 5:2 (4:1) |
| 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 |
| 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 1998, Qualifying tournament, Group 2 |
| 22.03.1998 | | Barbados | – | Saint Vincent and Grenadines | | 4:3 |
| 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 1996, Qualifying tournament, Group 6 |
| 28.04.1996 | | Barbados | – | Jamaica |  | 2:0 aet
(2:0),
pen. 3:4 |
| |
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, Qualifying tournament, Group 1 |
| 27.01.1994 | | Barbados | – | Grenada | | 4:2 aet
(2:0, 2:2) |
| 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 1992, Qualifying tournament, Group 1 |
| 27.03.1992 | | Barbados | – | Netherlands Antilles | | 1:0 |
| |
Caribbean Cup 1989, Final tournament, Group A |
| 03.07.1989 | | Barbados | – | Guadeloupe |  | 1:0 |
| Bridgetown |
