World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
 | 10.06.2025 |  | Costa Rica | | Trinidad and Tobago |  | |
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World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
 | 13.06.2017 |  | Costa Rica | | Trinidad and Tobago |  | 2:1 (2:1) |
| San José |
World Cup 2018, Qualifying tournament, CONCACAF, Fifth Round |
 | 11.11.2016 |  | Trinidad and Tobago | | Costa Rica |  | 0:2 (0:0) |
| Port of Spain |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
 | 10.10.2009 |  | Costa Rica | | Trinidad and Tobago |  | 4:0 (1:0) |
| San José |
World Cup 2010, Qualifying tournament, CONCACAF, Final Round |
 | 06.06.2009 |  | Trinidad and Tobago | | Costa Rica |  | 2:3 (1:1) |
| Bacolet |
Friendly internationals 2007 |
 | 04.02.2007 |  | Costa Rica | | Trinidad and Tobago |  | 4:0 (2:0) |
| Alajuela |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 07.09.2005 |  | Costa Rica | | Trinidad and Tobago |  | 2:0 (1:0) |
| San José |
World Cup 2006, Qualifying tournament, CONCACAF, Final Round |
 | 30.03.2005 |  | Trinidad and Tobago | | Costa Rica |  | 0:0 |
| Port of Spain |
CONCACAF Gold Cup 2002, Final tournament, Group C |
 | 20.01.2002 |  | Costa Rica | | Trinidad and Tobago |  | 1:1 (0:0) |
| Miami |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
 | 01.09.2001 |  | Trinidad and Tobago | | Costa Rica |  | 0:2 (0:2) |
| Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Final Round |
 | 28.03.2001 |  | Costa Rica | | Trinidad and Tobago |  | 3:0 (0:0) |
| Alajuela |
CONCACAF Gold Cup 2000, Final tournament, Quarterfinal |
 | 20.02.2000 |  | Costa Rica | | Trinidad and Tobago |  | 1:2 aet (0:1, 1:1) |
| San Diego |
Friendly internationals 2000 |
 | 26.01.2000 |  | Costa Rica | | Trinidad and Tobago |  | 2:1 (0:1) |
| San José |
Friendly internationals 1998 |
 | 29.01.1998 |  | Costa Rica | | Trinidad and Tobago |  | 4:0 (2:0) |
| San José |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 21.12.1996 |  | Costa Rica | | Trinidad and Tobago |  | 2:1 (2:1) |
| Cartago |
World Cup 1998, Qualifying tournament, CONCACAF, Semifinal round, group 1 |
 | 01.09.1996 |  | Trinidad and Tobago | | Costa Rica |  | 0:1 (0:0) |
| Port of Spain |
CONCACAF Gold Cup 1991, Final tournament, Group B |
 | 01.07.1991 |  | Costa Rica | | Trinidad and Tobago |  | 1:2 (1:1) |
| Pasadena |
CONCACAF Championship 1989, Final tournament, Final Round |
 | 11.06.1989 |  | Costa Rica | | Trinidad and Tobago |  | 1:0 (0:0) |
| San José |
CONCACAF Championship 1989, Final tournament, Final Round |
 | 28.05.1989 |  | Trinidad and Tobago | | Costa Rica |  | 1:1 (0:0) |
| Port of Spain |
Friendly internationals 1985 |
 | 18.07.1985 |  | Costa Rica | | Trinidad and Tobago |  | 3:1 |
| San José |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
 | 28.04.1985 |  | Costa Rica | | Trinidad and Tobago |  | 1:1 (0:1) |
| San José |
CONCACAF Championship 1985, Qualifying tournament, Second round, subgroup 3 |
 | 24.04.1985 |  | Costa Rica | | Trinidad and Tobago |  | 3:0 (1:0) |
| San José |
CONCACAF Championship 1971, Final tournament, Final Round |
 | 29.11.1971 |  | Trinidad and Tobago | | Costa Rica |  | 3:1 |
| Port of Spain |
CONCACAF Championship 1969, Final tournament, Final Round |
 | 04.12.1969 |  | Costa Rica | | Trinidad and Tobago |  | 5:0 (1:0) |
| San José |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
 | 07.03.1965 |  | Trinidad and Tobago | | Costa Rica |  | 0:1 (0:1) |
| Port of Spain |
World Cup 1966, Qualifying tournament, CONCACAF, First Round, Subgroup C |
 | 21.02.1965 |  | Costa Rica | | Trinidad and Tobago |  | 4:0 (1:0) |
| San José |
Friendly internationals 1965 |
 | 22.02.1965 |  | Costa Rica | | Trinidad and Tobago |  | 1:0 |
| San José |