Caribbean Championship 2017, Qualifying tournament, Fifth place playoff |
 | 08.01.2017 |  | Haiti | | Trinidad and Tobago |  | 4:3 aet (2:2, 2:2) |
| Couva |
Caribbean Championship 2017, Qualifying tournament, Fifth place playoff |
 | 04.01.2017 |  | Trinidad and Tobago | | Suriname |  | 1:2 aet (0:0, 1:1) |
| Couva |
Caribbean Championship 2017, Qualifying tournament, Third round, group 4 |
 | 11.10.2016 |  | Martinique | | Trinidad and Tobago |  | 2:0 aet (0:0) |
| Fort-de-France |
Caribbean Championship 2017, Qualifying tournament, Third round, group 4 |
 | 05.10.2016 |  | Trinidad and Tobago | | Dominican Republic |  | 4:0 (3:0) |
| Couva |
Caribbean Championship 2014, Final tournament, Final |
 | 18.11.2014 |  | Jamaica | | Trinidad and Tobago |  | 0:0 aet, pen. 4:3 |
| Montego Bay |
Caribbean Championship 2014, Final tournament, Group A |
 | 15.11.2014 |  | Cuba | | Trinidad and Tobago |  | 0:0 |
| Montego Bay |
Caribbean Championship 2014, Final tournament, Group A |
 | 13.11.2014 |  | Trinidad and Tobago | | French Guiana |  | 4:2 (1:0) |
| Montego Bay |
Caribbean Championship 2014, Final tournament, Group A |
 | 11.11.2014 |  | Curaçao | | Trinidad and Tobago |  | 2:3 (1:2) |
| Montego Bay |
Caribbean Championship 2014, Qualifying tournament, Second round, group 7 |
 | 12.10.2014 |  | Trinidad and Tobago | | Antigua and Barbuda |  | 1:0 (1:0) |
| Couva |
Caribbean Championship 2014, Qualifying tournament, Second round, group 7 |
 | 10.10.2014 |  | Trinidad and Tobago | | Saint Lucia |  | 2:0 (1:0) |
| Couva |
Caribbean Championship 2014, Qualifying tournament, Second round, group 7 |
 | 08.10.2014 |  | Trinidad and Tobago | | Dominican Republic |  | 6:1 (4:0) |
| Couva |
Caribbean Championship 2012, Final tournament, Final |
 | 16.12.2012 |  | Cuba | | Trinidad and Tobago |  | 1:0 aet (0:0) |
| St. John's |
Caribbean Championship 2012, Final tournament, Semifinal |
 | 14.12.2012 |  | Martinique | | Trinidad and Tobago |  | 1:1 aet (0:0, 1:1), pen. 4:5 |
| St. John's |
Caribbean Championship 2012, Final tournament, Group A |
 | 11.12.2012 |  | Trinidad and Tobago | | Dominican Republic |  | 2:1 (1:0) |
| St. John's |
Caribbean Championship 2012, Final tournament, Group A |
 | 09.12.2012 |  | Antigua and Barbuda | | Trinidad and Tobago |  | 2:0 (0:0) |
| St. John's |
Caribbean Championship 2012, Final tournament, Group A |
 | 07.12.2012 |  | Haiti | | Trinidad and Tobago |  | 0:0 |
| St. John's |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
 | 18.11.2012 |  | Trinidad and Tobago | | Cuba |  | 1:0 (0:0) |
| Bacolet |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
 | 16.11.2012 |  | Trinidad and Tobago | | Suriname |  | 3:0 (1:0) |
| Bacolet |
Caribbean Championship 2012, Qualifying tournament, Second round, group 8 |
 | 14.11.2012 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 1:1 (1:1) |
| Bacolet |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
 | 14.10.2012 |  | Anguilla | | Trinidad and Tobago |  | 0:10 (0:7) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
 | 12.10.2012 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:1 (0:0) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
 | 10.10.2012 |  | French Guiana | | Trinidad and Tobago |  | 1:4 (1:2) |
| Bassterre |
Caribbean Championship 2010, Final tournament, Group H |
 | 30.11.2010 |  | Martinique | | Trinidad and Tobago |  | 0:1 (0:0) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group H |
 | 28.11.2010 |  | Grenada | | Trinidad and Tobago |  | 1:0 (0:0) |
| Fort-de-France |
Caribbean Championship 2010, Final tournament, Group H |
 | 26.11.2010 |  | Trinidad and Tobago | | Cuba |  | 0:2 (0:1) |
| Fort-de-France |
Caribbean Championship 2010, Qualifying tournament, Second round, group F |
 | 06.11.2010 |  | Trinidad and Tobago | | Haiti |  | 4:0 (4:0) |
| San Fernando |
Caribbean Championship 2010, Qualifying tournament, Second round, group F |
 | 04.11.2010 |  | Trinidad and Tobago | | Guyana |  | 2:1 (2:0) |
| San Fernando |
Caribbean Championship 2010, Qualifying tournament, Second round, group F |
 | 02.11.2010 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 6:2 (2:2) |
| San Fernando |
Caribbean Championship 2008, Final tournament, Group A |
 | 07.12.2008 |  | Jamaica | | Trinidad and Tobago |  | 1:1 (0:0) |
| 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 |  | Trinidad and Tobago | | Grenada |  | 1:2 (0:1) |
| Kingston |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
 | 09.11.2008 |  | Trinidad and Tobago | | Guyana |  | 1:1 (0:0) |
| Macoya |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
 | 07.11.2008 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 3:1 (1:0) |
| Macoya |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
 | 05.11.2008 |  | Trinidad and Tobago | | Antigua and Barbuda |  | 3:2 (0:1) |
| Macoya |
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, Semifinal |
 | 20.01.2007 |  | Trinidad and Tobago | | Cuba |  | 3:1 (1:0) |
| 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 |
Caribbean Cup 2007, Final tournament, Sedley Joseph Group |
 | 15.01.2007 |  | Trinidad and Tobago | | Martinique |  | 5:1 (2:1) |
| Port of Spain |
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 |
Caribbean Cup 2005, Final tournament, Final Round |
 | 22.02.2005 |  | Trinidad and Tobago | | Cuba |  | 1:2 (1:1) |
| Bridgetown |
Caribbean Cup 2005, Final tournament, Final Round |
 | 20.02.2005 |  | Jamaica | | Trinidad and Tobago |  | 2:1 (2:1) |
| Bridgetown |
Caribbean Cup 2005, Qualifying tournament, Third round |
 | 16.01.2005 |  | Saint Vincent and Grenadines | | Trinidad and Tobago |  | 1:0 (0:0) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Third round |
 | 09.01.2005 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 3:1 (0:1) |
| San Fernando |
Caribbean Cup 2005, Qualifying tournament, Second round |
 | 19.12.2004 |  | Trinidad and Tobago | | British Virgin Islands |  | 2:0 (1:0) |
| Port of Spain |
Caribbean Cup 2005, Qualifying tournament, Second round |
 | 12.12.2004 |  | British Virgin Islands | | Trinidad and Tobago |  | 0:4 (0:1) |
| Road Town |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 28.11.2004 |  | Trinidad and Tobago | | Suriname |  | 1:0 (0:0) |
| Malabar |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 26.11.2004 |  | Trinidad and Tobago | | Grenada |  | 2:0 (1:0) |
| San Fernando |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 24.11.2004 |  | Trinidad and Tobago | | Puerto Rico |  | 5:0 (2:0) |
| Macoya |
Caribbean Cup 2001, Final tournament, Final |
 | 25.05.2001 |  | Trinidad and Tobago | | Haiti |  | 3:0 (1:0) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Semifinal |
 | 22.05.2001 |  | Trinidad and Tobago | | Cuba |  | 2:0 (2:0) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Group 1 |
 | 19.05.2001 |  | Trinidad and Tobago | | Martinique |  | 1:2 (1:1) |
| Port of Spain |
Caribbean Cup 2001, Final tournament, Group 1 |
 | 17.05.2001 |  | Trinidad and Tobago | | Jamaica |  | 2:1 (0:1) |
| 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, Final tournament, Final |
 | 13.06.1999 |  | Trinidad and Tobago | | Cuba |  | 2:1 aet (0:0, 1:1) |
| 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 1999, Final tournament, Group A |
 | 07.06.1999 |  | Trinidad and Tobago | | Guadeloupe |  | 3:2 (1:1) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Group A |
 | 05.06.1999 |  | Trinidad and Tobago | | Grenada |  | 7:0 (5:0) |
| Port of Spain |
Caribbean Cup 1999, Final tournament, Group A |
 | 03.06.1999 |  | Trinidad and Tobago | | Jamaica |  | 1:0 (1:0) |
| Port of Spain |
Caribbean Cup 1998, Final tournament, Final |
 | 31.07.1998 |  | Trinidad and Tobago | | Jamaica |  | 1:2 (0:2) |
| Trinidad and Tobago |
Caribbean Cup 1998, Final tournament, Semifinal |
 | 29.07.1998 |  | Trinidad and Tobago | | Haiti |  | 4:1 (3:0) |
| Trinidad and Tobago |
Caribbean Cup 1998, Final tournament, Group A |
 | 26.07.1998 |  | Trinidad and Tobago | | Dominica |  | 8:0 |
| |
Caribbean Cup 1998, Final tournament, Group A |
 | 24.07.1998 |  | Trinidad and Tobago | | Martinique |  | 2:1 |
| |
Caribbean Cup 1998, Final tournament, Group A |
 | 22.07.1998 |  | Trinidad and Tobago | | Antigua and Barbuda |  | 3:2 |
| |
Caribbean Cup 1997, Final tournament, Final |
 | 13.07.1997 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:4 (0:2) |
| Bassterre |
Caribbean Cup 1997, Final tournament, Semifinal |
 | 10.07.1997 |  | Trinidad and Tobago | | Jamaica |  | 1:1 aet (1:0, 1:1), pen. 4:2 |
| St. Kitts and Nevis, Bassterre |
Caribbean Cup 1997, Final tournament, Group B |
 | 08.07.1997 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:3 (0:3) |
| Bassterre |
Caribbean Cup 1997, Final tournament, Group B |
 | 04.07.1997 |  | Trinidad and Tobago | | Martinique |  | 1:2 (1:1) |
| Bassterre |
Caribbean Cup 1997, Qualifying tournament, Group 3 |
 | 06.04.1997 |  | Trinidad and Tobago | | Grenada |  | 2:3 (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 1997, Qualifying tournament, Group 3 |
 | 02.04.1997 |  | Trinidad and Tobago | | Guyana |  | 3:0 (1:0) |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Final |
 | 07.06.1996 |  | Trinidad and Tobago | | Cuba |  | 2:0 |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Semifinal |
 | 02.06.1996 |  | Trinidad and Tobago | | Martinique |  | 2:1 aet (0:0, 1:1) |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
 | 28.05.1996 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 5:1 |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
 | 26.05.1996 |  | Trinidad and Tobago | | Suriname |  | 3:0 |
| Palo Seco |
Caribbean Cup 1996, Final tournament, Group A |
 | 24.05.1996 |  | Trinidad and Tobago | | Jamaica |  | 1:0 |
| Port of Spain |
Caribbean Cup 1995, Final tournament, Final |
 | 30.07.1995 |  | Saint Vincent and Grenadines | | Trinidad and Tobago |  | 0:5 (0:2) |
| Cayman Islands |
Caribbean Cup 1995, Final tournament, Semifinal |
 | 28.07.1995 |  | Cayman Islands | | Trinidad and Tobago |  | 2:9 (1:2) |
| Cayman Islands |
Caribbean Cup 1995, Final tournament, Group B |
 | 23.07.1995 |  | Jamaica | | Trinidad and Tobago |  | 1:0 (1:0) |
| Kingston |
Caribbean Cup 1995, Final tournament, Group B |
 | 21.07.1995 |  | Saint Lucia | | Trinidad and Tobago |  | 0:5 (0:3) |
| Montego Bay |
Caribbean Cup 1995, Final tournament, Group B |
 | 19.07.1995 |  | Trinidad and Tobago | | Cuba |  | 2:0 (1:0) |
| Kingston |
Caribbean Cup 1994, Final tournament, Final |
 | 17.04.1994 |  | Trinidad and Tobago | | Martinique |  | 7:2 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Semifinal |
 | 14.04.1994 |  | Trinidad and Tobago | | Suriname |  | 3:2 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
 | 11.04.1994 |  | Trinidad and Tobago | | Dominica |  | 5:0 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
 | 09.04.1994 |  | Trinidad and Tobago | | Barbados |  | 2:0 |
| Port of Spain |
Caribbean Cup 1994, Final tournament, Group A |
 | 07.04.1994 |  | Trinidad and Tobago | | Guadeloupe |  | 0:0 |
| Port of Spain |
Caribbean Cup 1993, Final tournament, 3rd place match |
 | 30.05.1993 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 3:2 |
| Kingston |
Caribbean Cup 1993, Final tournament, Semifinal |
 | 28.05.1993 |  | Jamaica | | Trinidad and Tobago |  | 3:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group B |
 | 25.05.1993 |  | Martinique | | Trinidad and Tobago |  | 3:2 |
| Montego Bay |
Caribbean Cup 1993, Final tournament, Group B |
 | 25.05.1993 |  | Trinidad and Tobago | | Saint Vincent and Grenadines |  | 4:1 |
| Montego Bay |
Caribbean Cup 1993, Final tournament, Group B |
 | 23.05.1993 |  | Trinidad and Tobago | | Saint Lucia |  | 1:1 |
| Montego Bay |
Caribbean Cup 1992, Final tournament, Final |
 | 27.06.1992 |  | Trinidad and Tobago | | Jamaica |  | 3:1 (2:0) |
| Port of Spain |
Caribbean Cup 1992, Final tournament, Semifinal |
 | 24.06.1992 |  | Trinidad and Tobago | | Cuba |  | 1:0 |
| |
Caribbean Cup 1992, Final tournament, Group A |
 | 21.06.1992 |  | Trinidad and Tobago | | Antigua and Barbuda |  | 7:0 |
| |
Caribbean Cup 1992, Final tournament, Group A |
 | 19.06.1992 |  | Trinidad and Tobago | | Suriname |  | 1:0 |
| |
Caribbean Cup 1992, Final tournament, Group A |
 | 17.06.1992 |  | Trinidad and Tobago | | Martinique |  | 2:1 |
| |
Caribbean Cup 1991, Final tournament, Final |
 | 02.06.1991 |  | Jamaica | | Trinidad and Tobago |  | 2:0 (1:0) |
| Kingston |
Caribbean Cup 1991, Final tournament, Semifinal |
 | 30.05.1991 |  | Trinidad and Tobago | | Guyana |  | 3:1 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group B |
 | 27.05.1991 |  | Trinidad and Tobago | | Dominican Republic |  | 7:0 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group B |
 | 25.05.1991 |  | Trinidad and Tobago | | Martinique |  | 1:0 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group B |
 | 23.05.1991 |  | Trinidad and Tobago | | Saint Lucia |  | 1:2 |
| Kingston |
Caribbean Cup 1989, Final tournament, Final |
 | 09.07.1989 |  | Trinidad and Tobago | | Grenada |  | 2:1 |
| Bridgetown |
Caribbean Cup 1989, Final tournament, Group A |
 | 07.07.1989 |  | Trinidad and Tobago | | Guadeloupe |  | 0:2 |
| Bridgetown |
Caribbean Cup 1989, Final tournament, Group A |
 | 05.07.1989 |  | Barbados | | Trinidad and Tobago |  | 0:3 |
| Bridgetown |
Caribbean Cup 1989, Qualifying tournament, Zone A |
 | ??.06.1989 |  | Trinidad and Tobago | | Aruba |  | 11:0 |
| |
Caribbean Cup 1989, Qualifying tournament, Zone A |
 | ??.06.1989 |  | Trinidad and Tobago | | French Guiana |  | 3:1 |
| |
Caribbean Cup 1989, Qualifying tournament, Zone A |
 | ??.06.1989 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 2:0 |
| |
Caribbean Cup 1989, Qualifying tournament, Zone A |
 | 06.06.1989 |  | Grenada | | Trinidad and Tobago |  | 1:0 |
| |