Head to Head
| 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
| 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 |
| CONCACAF Nations League | 2024/09/11 02:00 | Honduras v Jamaica | W | 1-2 |
| CONCACAF Nations League | 2024/09/07 00:00 | Jamaica v Cuba | D | 0-0 |
| Copa America | 2024/07/01 00:00 | Jamaica v Venezuela | L | 0-3 |
Away History
| 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 |
| CONCACAF Nations League | 2024/09/07 02:00 | Honduras v Trinidad & Tobago | L | 4-0 |
| North & Central America - World Cup Qualifying | 2024/06/08 21:30 | Bahamas v Trinidad & Tobago | W | 1-7 |
| North & Central America - World Cup Qualifying | 2024/06/05 23:30 | Trinidad & Tobago v Grenada | D | 2-2 |