World Cup 2026, Qualifying tournament, CONCACAF, Third Round, Group B |
 | 13.11.2025 |  | Trinidad and Tobago | – | Jamaica |  | 1:1 (0:0) |
| Port of Spain |
World Cup 2026, Qualifying tournament, CONCACAF, Third Round, Group B |
| 09.09.2025 | | Jamaica | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kingston |
Friendly internationals 2025 |
| 27.05.2025 | | Jamaica | – | Trinidad and Tobago | | 3:2 (1:0) |
| England, London |
Friendly internationals 2025 |
| 09.02.2025 | | Jamaica | – | Trinidad and Tobago | | 1:1 (0:1) |
| Kingston |
Friendly internationals 2025 |
| 06.02.2025 | | Jamaica | – | Trinidad and Tobago | | 1:0 (0:0) |
| Montego Bay |
Friendly internationals 2024 |
| 03.03.2024 | | Trinidad and Tobago | – | Jamaica | | 0:0 |
| Malabar |
Friendly internationals 2024 |
| 01.03.2024 | | Trinidad and Tobago | – | Jamaica | | 0:1 (0:0) |
| Port of Spain |
CONCACAF Gold Cup 2023, Final tournament, Group A |
| 28.06.2023 | | Jamaica | – | Trinidad and Tobago | | 4:1 (3:0) |
| Saint Louis |
Friendly internationals 2023 |
| 14.03.2023 | | Jamaica | – | Trinidad and Tobago | | 0:0 |
| Kingston |
Friendly internationals 2023 |
| 11.03.2023 | | Jamaica | – | Trinidad and Tobago | | 0:1 (0:0) |
| Montego Bay |
Friendly internationals 2017 |
| 24.08.2017 | | Trinidad and Tobago | – | Jamaica | | 1:2 (1:1) |
| Port of Spain |
Caribbean Championship 2014, Final tournament, Final |
| 18.11.2014 | | Jamaica | – | Trinidad and Tobago | | 0:0 aet,
pen. 4:3 |
| Montego Bay |
Friendly internationals 2013 |
| 19.11.2013 | | Trinidad and Tobago | – | Jamaica | | 2:0 (0:0) |
| Port of Spain |
Friendly internationals 2013 |
| 15.11.2013 | | Jamaica | – | Trinidad and Tobago | | 0:1 (0:1) |
| Montego Bay |
Friendly internationals 2010 |
| 10.10.2010 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
Friendly internationals 2010 |
| 11.08.2010 | | Trinidad and Tobago | – | Jamaica | | 1:3 (1:2) |
| Macoya |
Caribbean Championship 2008, Final tournament, Group A |
| 07.12.2008 | | Jamaica | – | Trinidad and Tobago | | 1:1 (0:0) |
| Trelawny |
Friendly internationals 2008 |
| 07.06.2008 | | Trinidad and Tobago | – | Jamaica | | 1:1 (1:0) |
| Macoya |
Friendly internationals 2008 |
| 26.03.2008 | | Jamaica | – | Trinidad and Tobago | | 2:2 (2:0) |
| Kingston |
Caribbean Cup 2005, Final tournament, Final Round |
| 20.02.2005 | | Jamaica | – | Trinidad and Tobago | | 2:1 (2:1) |
| Bridgetown |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 30.06.2001 | | Trinidad and Tobago | – | Jamaica | | 1:2 (1:1) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
| 28.02.2001 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
Caribbean Cup 2001, Final tournament, Group 1 |
| 17.05.2001 | | Trinidad and Tobago | – | Jamaica | | 2:1 (0:1) |
| Port of Spain |
Friendly internationals 2000 |
| 08.07.2000 | | Trinidad and Tobago | – | Jamaica | | 2:4 (1:2) |
| |
Caribbean Cup 1999, Final tournament, Group A |
| 03.06.1999 | | Trinidad and Tobago | – | Jamaica | | 1:0 (1:0) |
| Port of Spain |
Friendly internationals 1999 |
| 28.03.1999 | | Trinidad and Tobago | – | Jamaica | | 2:0 (1:0) |
| |
Caribbean Cup 1998, Final tournament, Final |
| 31.07.1998 | | Trinidad and Tobago | – | Jamaica | | 1:2 (0:2) |
| Trinidad and Tobago |
Friendly internationals 1998 |
| 07.01.1998 | | Trinidad and Tobago | – | Jamaica | | 0:0 |
| |
Friendly internationals 1997 |
| 23.11.1997 | | Trinidad and Tobago | – | Jamaica | | 0:0 |
| |
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 |
Friendly internationals 1997 |
| 01.05.1997 | | Trinidad and Tobago | – | Jamaica | | 1:1 |
| |
Caribbean Cup 1996, Final tournament, Group A |
| 24.05.1996 | | Trinidad and Tobago | – | Jamaica | | 1:0 |
| Port of Spain |
Friendly internationals 1995 |
| 20.10.1995 | | Trinidad and Tobago | – | Jamaica | | 0:1 (0:0) |
| Cayman Islands |
Friendly internationals 1995 |
| 24.09.1995 | | Trinidad and Tobago | – | Jamaica | | 1:0 (0:0) |
| |
Friendly internationals 1995 |
| 06.08.1995 | | Jamaica | – | Trinidad and Tobago | | 1:0 (0:0) |
| Canada |
Caribbean Cup 1995, Final tournament, Group B |
| 23.07.1995 | | Jamaica | – | Trinidad and Tobago | | 1:0 (1:0) |
| Kingston |
World Cup 1994, Qualifying tournament, CONCACAF, First Round |
| 18.08.1992 | | Jamaica | – | Trinidad and Tobago | | 1:1 (1:1) |
| Kingston |
World Cup 1994, Qualifying tournament, CONCACAF, First Round |
| 05.07.1992 | | Trinidad and Tobago | – | Jamaica | | 1:2 (0:0) |
| Port of Spain |
Caribbean Cup 1993, Final tournament, Semifinal |
| 28.05.1993 | | Jamaica | – | Trinidad and Tobago | | 3:0 |
| Kingston |
Caribbean Cup 1992, Final tournament, Final |
| 27.06.1992 | | Trinidad and Tobago | – | Jamaica | | 3:1 (2:0) |
| Port of Spain |
Caribbean Cup 1991, Final tournament, Final |
| 02.06.1991 | | Jamaica | – | Trinidad and Tobago | | 2:0 (1:0) |
| Kingston |
CONCACAF Championship 1969, Final tournament, Final Round |
| 30.11.1969 | | Trinidad and Tobago | – | Jamaica | | 3:2 (2:2) |
| San José |
CONCACAF Championship 1967, Qualifying tournament, Group 1 |
| 18.01.1967 | | Jamaica | – | Trinidad and Tobago | | 1:1 |
| Kingston |
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