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 |