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 |
| |
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