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 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, First Round, Group 3 |
| 05.09.2014 |  | Martinique | – | Barbados | | 3:2 (0:2) |
| Fort-de-France |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 4 |
| 25.09.2012 | | Barbados | – | Dominican Republic | | 0:1 (0:0) |
| Bridgetown |
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 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 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 1999, Qualifying tournament, Group 2 |
| 14.03.1999 |  | Guadeloupe | – | Barbados | | 1:0 |
| Pointe-à-Pitre |
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 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 1994, Final tournament, Group A |
| 09.04.1994 | | Trinidad and Tobago | – | Barbados | | 2:0 |
| Port of Spain |
Caribbean Cup 1994, Qualifying tournament, Group 1 |
| 23.01.1994 | | Barbados | – | Puerto Rico |  | 0:1 |
| Bridgetown |
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 1989, Final tournament, Group A |
| 05.07.1989 | | Barbados | – | Trinidad and Tobago | | 0:3 |
| Bridgetown |
