All-time head-to-head

1. WJun 10, 20252–1HFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Jeyland Mitchell 23', Warren Madrigal 38'

   Trinidad and Tobago: Levi García 58'

2. WJun 13, 20172–1HFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Francisco Calvo 1', Bryan Ruiz 44'

   Trinidad and Tobago: Kevin Molino 35'

3. WNov 11, 20162–0AFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Christian Bolaños 65', Rónald Matarrita 90'

   Trinidad and Tobago: —

4. WOct 10, 20094–0HFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Julius James 26' (OG), Walter Centeno 51', Álvaro Saborío 61', Álvaro Saborío 64'

   Trinidad and Tobago: —

5. WJun 6, 20093–2AFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Álvaro Saborío 40', Celso Borges 52', Celso Borges 68'

   Trinidad and Tobago: Carlos Edwards 29', Collin Samuel 63'

6. WFeb 4, 20074–0HFriendly
   Friendly
7. WSep 7, 20052–0HFIFA World Cup qualification
   FIFA World Cup qualification

   Costa Rica: Álvaro Saborío 15', Walter Centeno 50'

   Trinidad and Tobago: —

8. DMar 30, 20050–0AFIFA World Cup qualification
   FIFA World Cup qualification
9. DJan 20, 20021–1NGold Cup
   Gold Cup

   Costa Rica: Rolando Fonseca 56'

   Trinidad and Tobago: Stern John 90'

10. WSep 1, 20012–0AFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Rónald Gómez 4', Rónald Gómez 35'

    Trinidad and Tobago: —

11. WMar 25, 20013–0HFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Steven Bryce 46', Paulo Wanchope 81', Paulo Wanchope 88'

    Trinidad and Tobago: —

12. LFeb 20, 20001–2NGold Cup
    Gold Cup

    Costa Rica: Paulo Wanchope 89'

    Trinidad and Tobago: Arnold Dwarika 26', Mickey Trotman 101'

13. WJan 26, 20002–1HFriendly
    Friendly
14. WDec 21, 19962–1HFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Paulo Wanchope 44', Paulo Wanchope 60'

    Trinidad and Tobago: Jerren Nixon 7'

15. WSep 1, 19961–0AFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Rónald Gómez 54'

    Trinidad and Tobago: —

16. LJul 1, 19911–2NGold Cup
    Gold Cup

    Costa Rica: Hernán Medford 6'

    Trinidad and Tobago: Leonson Lewis 38', Alvin Thomas 89'

17. WJun 11, 19891–0HCONCACAF Championship
    CONCACAF Championship

    Costa Rica: Juan Cayasso 2'

    Trinidad and Tobago: —

18. DMay 28, 19891–1ACONCACAF Championship
    CONCACAF Championship

    Costa Rica: Evaristo Coronado 69'

    Trinidad and Tobago: Philibert Jones 13'

19. WJul 18, 19853–1HFriendly
    Friendly
20. DApr 28, 19851–1HCONCACAF Championship
    CONCACAF Championship

    Costa Rica: Jorge Manuel Ulate 57'

    Trinidad and Tobago: Nevick De Noon 18'

21. WApr 24, 19853–0HCONCACAF Championship
    CONCACAF Championship

    Costa Rica: Franklin Williams 15', Miguel Lacey 65', Nilton Nóbrega 79'

    Trinidad and Tobago: —

22. LDec 5, 19711–3ACONCACAF Championship
    CONCACAF Championship

    Costa Rica: Emilio Valle 24'

    Trinidad and Tobago: Aubert Philips 30', Steve David 58', Anthony Douglas 69'

23. WDec 4, 19695–0HCONCACAF Championship
    CONCACAF Championship

    Costa Rica: Víctor Ruiz 10', Víctor Ruiz 55', Víctor Ruiz 65', Víctor Ruiz 70', Wálter Elizondo 85' (pen.)

    Trinidad and Tobago: —

24. WMar 7, 19651–0AFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Leonel Hernández 29'

    Trinidad and Tobago: —

25. WFeb 22, 19651–0HFriendly
    Friendly
26. WFeb 21, 19654–0HFIFA World Cup qualification
    FIFA World Cup qualification

    Costa Rica: Leonel Hernández 28' (pen.), Leonel Hernández 50', Errol Daniels 80', Edgar Marín 84'

    Trinidad and Tobago: —

Source: martj42/international_results — international matches from 1872 to today (MIT-licensed open dataset). Predecessor teams follow FIFA attribution (Yugoslavia → Serbia, Czechoslovakia → Czechia).