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Friendly International 
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Previous matches:
| Trinidad and Tobago | 0 | 0 | Jamaica |
| Friendly Match - 03.03.2024 | |||
| Trinidad and Tobago | 0 | 1 | Jamaica |
| Friendly Match - 01.03.2024 | |||
| Jamaica | 4 | 1 | Trinidad and Tobago |
| Concacaf Gold Cup - 28.06.2023 | |||
| Jamaica | 0 | 0 | Trinidad and Tobago |
| Friendly Match - 15.03.2023 | |||
| Jamaica | 0 | 1 | Trinidad and Tobago |
| Friendly Match - 11.03.2023 | |||
| Trinidad and Tobago | 1 | 2 | Jamaica |
| Friendly Match - 25.08.2017 | |||
| Trinidad and Tobago | 2 | 0 | Jamaica |
| Friendly Match - 20.11.2013 | |||
| Jamaica | 0 | 1 | Trinidad and Tobago |
| Friendly Match - 16.11.2013 | |||
| Jamaica | 1 | 0 | Trinidad and Tobago |
| Friendly Match - 10.10.2010 | |||
| Trinidad and Tobago | 1 | 3 | Jamaica |
| Friendly Match - 11.08.2010 | |||
| Trinidad and Tobago | 1 | 1 | Jamaica |
| Friendly Match - 06.06.2008 | |||
| Jamaica | 2 | 2 | Trinidad and Tobago |
| Friendly Match - 27.03.2008 | |||
| Trinidad and Tobago | 1 | 2 | Jamaica |
| WC Qualifying CONCACAF - 29.06.2001 | |||
| Jamaica | 1 | 0 | Trinidad and Tobago |
| WC Qualifying CONCACAF - 27.02.2001 | |||
| Jamaica | 1 | 1 | Trinidad and Tobago |
| WC Qualifying CONCACAF - 15.08.1992 | |||
| Trinidad and Tobago | 1 | 2 | Jamaica |
| WC Qualifying CONCACAF - 04.07.1992 | |||