Head to Head
| International Match | 2025/02/10 01:00 | Jamaica v Trinidad & Tobago | D | 1-1 |
| International Match | 2025/02/07 00:30 | Jamaica v Trinidad & Tobago | W | 1-0 |
| International Match | 2024/03/03 20:00 | Trinidad & Tobago v Jamaica | D | 0-0 |
| CONCACAF Gold Cup | 2023/06/28 23:30 | Jamaica v Trinidad & Tobago | W | 4-1 |
| International Match | 2023/03/15 00:00 | Jamaica v Trinidad & Tobago | D | 0-0 |
| International Match | 2023/03/11 23:00 | Jamaica v Trinidad & Tobago | L | 0-1 |
| International Match | 2017/08/25 00:00 | Trinidad & Tobago v Jamaica | W | 1-2 |
Home History
| CONCACAF Gold Cup Qualifying | 2025/03/26 00:00 | Jamaica v St. Vincent/Grenadines | W | 3-0 |
| CONCACAF Gold Cup Qualifying | 2025/03/21 23:00 | St. Vincent/Grenadines v Jamaica | D | 1-1 |
| International Match | 2025/02/10 01:00 | Jamaica v Trinidad & Tobago | D | 1-1 |
| International Match | 2025/02/07 00:30 | Jamaica v Trinidad & Tobago | W | 1-0 |
| CONCACAF Nations League | 2024/11/19 01:00 | USA v Jamaica | L | 4-2 |
| CONCACAF Nations League | 2024/11/15 01:00 | Jamaica v USA | L | 0-1 |
| CONCACAF Nations League | 2024/10/15 01:00 | Jamaica v Honduras | D | 0-0 |
| CONCACAF Nations League | 2024/10/11 02:00 | Nicaragua v Jamaica | W | 0-2 |
Away History
| CONCACAF Gold Cup Qualifying | 2025/03/25 23:00 | Trinidad & Tobago v Cuba | W | 4-0 |
| CONCACAF Gold Cup Qualifying | 2025/03/21 20:00 | Cuba v Trinidad & Tobago | W | 1-2 |
| International Match | 2025/02/10 01:00 | Jamaica v Trinidad & Tobago | D | 1-1 |
| International Match | 2025/02/07 00:30 | Jamaica v Trinidad & Tobago | L | 1-0 |
| International Match | 2024/12/17 13:15 | Saudi Arabia v Trinidad & Tobago | L | 3-1 |
| CONCACAF Nations League | 2024/10/15 01:00 | Trinidad & Tobago v Cuba | W | 3-1 |
| CONCACAF Nations League | 2024/10/10 20:00 | Cuba v Trinidad & Tobago | D | 2-2 |
| CONCACAF Nations League | 2024/09/10 23:00 | Trinidad & Tobago v French Guiana | D | 0-0 |