Caribbean Championship 2017, Qualifying tournament, Fifth place playoff |
 | 08.01.2017 |  | Haiti | – | Trinidad and Tobago |  | 4:3 aet
(2:2, 2:2) |
| Couva |
Copa América Centenario 2016 (commemorative), Qualifying play-offs, Play-off |
| 08.01.2016 | | Trinidad and Tobago | – | Haiti | | 0:1 (0:1) |
| Ciudad de Panamá |
CONCACAF Gold Cup 2013, Final tournament, Group B |
| 12.07.2013 | | Trinidad and Tobago | – | Haiti | | 0:2 (0:1) |
| Miami |
Caribbean Championship 2012, Final tournament, Group A |
| 07.12.2012 | | Haiti | – | Trinidad and Tobago | | 0:0 |
| St. John's |
Caribbean Championship 2010, Qualifying tournament, Second round, group F |
| 06.11.2010 | | Trinidad and Tobago | – | Haiti | | 4:0 (4:0) |
| San Fernando |
Friendly internationals 2008 |
| 10.08.2008 | | Haiti | – | Trinidad and Tobago | | 1:0 (0:0) |
| Port-au-Prince |
Friendly internationals 2008 |
| 30.07.2008 | | Trinidad and Tobago | – | Haiti | | 2:0 (0:0) |
| Macoya |
Friendly internationals 2007 |
| 28.05.2007 | | Trinidad and Tobago | – | Haiti | | 1:0 (0:0) |
| Port of Spain |
Caribbean Cup 2007, Final tournament, Final |
| 23.01.2007 | | Trinidad and Tobago | – | Haiti | | 1:2 (0:1) |
| Port of Spain |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
| 17.01.2007 | | Trinidad and Tobago | – | Haiti | | 3:1 (1:0) |
| Port of Spain |
Friendly internationals 2005 |
| 06.02.2005 | | Trinidad and Tobago | – | Haiti | | 0:1 (0:1) |
| Scarborough Shaw Park Stadium |
Friendly internationals 2005 |
| 03.02.2005 | | Trinidad and Tobago | – | Haiti | | 2:1 (2:0) |
| Port of Spain |
Friendly internationals 2005 |
| 01.02.2005 | | Trinidad and Tobago | – | Haiti | | 1:0 (0:0) |
| Port of Spain |
Friendly internationals 2003 |
| 31.07.2003 | | Haiti | – | Trinidad and Tobago | | 2:0 (0:0) |
| St. Kitts and Nevis |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 3 |
| 19.05.2000 | | Haiti | – | Trinidad and Tobago | | 1:1 (0:1) |
| Port-au-Prince |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 3 |
| 07.05.2000 | | Trinidad and Tobago | – | Haiti | | 3:1 (1:0) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Final |
| 25.05.2001 | | Trinidad and Tobago | – | Haiti | | 3:0 (1:0) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Semifinal |
| 11.06.1999 | | Trinidad and Tobago | – | Haiti | | 6:1 (1:0) |
| Port of Spain |
Caribbean Cup 1998, Final tournament, Semifinal |
| 29.07.1998 | | Trinidad and Tobago | – | Haiti | | 4:1 (3:0) |
| Trinidad and Tobago |
Friendly internationals 1996 |
| 06.03.1996 | | Trinidad and Tobago | – | Haiti | | 2:0 (2:0) |
| |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 17.08.1980 | | Trinidad and Tobago | – | Haiti | | 1:0 (0:0) |
| San Fernando |
CONCACAF Championship 1981, Qualifying tournament, Caribbean Zone, subgroup B |
| 01.08.1980 | | Haiti | – | Trinidad and Tobago | | 2:0 (0:0) |
| Port-au-Prince |
CONCACAF Championship 1973, Final tournament, Final Round |
| 04.12.1973 | | Haiti | – | Trinidad and Tobago | | 2:1 (1:1) |
| Port-au-Prince |
CONCACAF Championship 1971, Final tournament, Final Round |
| 05.12.1971 | | Trinidad and Tobago | – | Haiti | | 0:6 |
| Port of Spain |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 25.11.1968 | | Haiti | – | Trinidad and Tobago | | 2:4 (1:2) |
| Port-au-Prince |
World Cup 1970, Qualifying tournament, CONCACAF, First Round, Subgroup B |
| 23.11.1968 | | Haiti | – | Trinidad and Tobago | | 4:0 (1:0) |
| Port-au-Prince |
CONCACAF Championship 1967, Final tournament, Final Round |
| 08.03.1967 | | Trinidad and Tobago | – | Haiti | | 3:2 (2:1) |
| Tegucigalpa |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 11.01.1967 | | Haiti | – | Trinidad and Tobago | | 4:2 |
| Kingston |
