Friendly internationals 2022 |
 | 25.03.2022 |  | Trinidad and Tobago | – | Barbados |  | 9:0 (4:0) |
| Port of Spain |
Friendly internationals 2017 |
| 10.03.2017 | | Trinidad and Tobago | – | Barbados | | 2:0 (2:0) |
| Couva |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
| 11.10.2011 | | Trinidad and Tobago | – | Barbados | | 4:0 (1:0) |
| Port of Spain |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group B |
| 06.09.2011 | | Barbados | – | Trinidad and Tobago | | 0:2 (0:1) |
| Bridgetown |
Caribbean Championship 2008, Final tournament, Group A |
| 05.12.2008 | | Barbados | – | Trinidad and Tobago | | 1:2 (1:1) |
| Montego Bay |
Friendly internationals 2008 |
| 11.05.2008 | | Trinidad and Tobago | – | Barbados | | 3:0 (1:0) |
| Macoya |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
| 12.01.2007 | | Trinidad and Tobago | – | Barbados | | 1:1 (1:0) |
| Port of Spain |
Caribbean Cup 2005, Final tournament, Final Round |
| 24.02.2005 | | Barbados | – | Trinidad and Tobago | | 2:3 (1:2) |
| Bridgetown |
Friendly internationals 2002 |
| 25.07.2002 | | Trinidad and Tobago | – | Barbados | | 0:0 |
| St. Kitts and Nevis |
Caribbean Cup 2001, Final tournament, Group 1 |
| 15.05.2001 | | Trinidad and Tobago | – | Barbados | | 5:0 (2:0) |
| Malabar |
Friendly internationals 2000 |
| 29.06.2000 | | Barbados | – | Trinidad and Tobago | | 0:0 |
| |
Friendly internationals 1998 |
| 05.01.1998 | | Barbados | – | Trinidad and Tobago | | 0:1 (0:0) |
| |
Friendly internationals 1997 |
| 02.07.1997 | | Barbados | – | Trinidad and Tobago | | 1:1 |
| |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
| 04.04.1997 | | Trinidad and Tobago | – | Barbados | | 0:1 (0:1) |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
| 09.04.1994 | | Trinidad and Tobago | – | Barbados | | 2:0 |
| Port of Spain |
World Cup 1994, Qualifying tournament, CONCACAF, Second preliminary round |
| 31.05.1992 | | Trinidad and Tobago | – | Barbados | | 3:0 (0:0) |
| Port of Spain |
World Cup 1994, Qualifying tournament, CONCACAF, Second preliminary round |
| 19.04.1992 | | Barbados | – | Trinidad and Tobago | | 1:2 (0:1) |
| Bridgetown |
Caribbean Cup 1989, Final tournament, Group A |
| 05.07.1989 | | Barbados | – | Trinidad and Tobago | | 0:3 |
| Bridgetown |
Olympic Games 1988, Qualifying tournament, CONCACAF, First Round |
| 24.05.1987 | | Barbados | – | Trinidad and Tobago | | 1:1 |
| |
Olympic Games 1988, Qualifying tournament, CONCACAF, First Round |
| 10.05.1987 | | Trinidad and Tobago | – | Barbados | | 2:0 |
| |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 14.09.1976 | | Barbados | – | Trinidad and Tobago | | 1:3 (1:1) * |
| Bridgetown |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 31.08.1976 | | Trinidad and Tobago | – | Barbados | | 1:0 (1:0) |
| Port of Spain |
CONCACAF Championship 1977, Qualifying tournament, Caribbean Zone, Subgroup A, Round 1 |
| 15.08.1976 | | Barbados | – | Trinidad and Tobago | | 2:1 (0:0) |
| Bridgetown |
Olympic Games 1976, Qualifying tournament, CONCACAF, Preliminary Round |
| | | Trinidad and Tobago | – | Barbados | | 0:0 |
| |
Olympic Games 1976, Qualifying tournament, CONCACAF, Preliminary Round |
| | | Barbados | – | Trinidad and Tobago | | 1:1 |
| |
Olympic Games 1976, Qualifying tournament, CONCACAF, Preliminary Round |
| | | Barbados | – | Trinidad and Tobago | | 1:3 * |
| |
Central American and Caribbean Games 1974, Group A |
| 02.03.1974 | | Trinidad and Tobago | – | Barbados | | 1:0 * |
| Santo Domingo de Guzmán |
