Head to Head
| CONCACAF Gold Cup | 2023/06/28 23:30 | Jamaica v Trinidad & Tobago | L | 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 | W | 0-1 |
| International Match | 2017/08/25 00:00 | Trinidad & Tobago v Jamaica | L | 1-2 |
Home History
| CONCACAF Nations League | 2023/11/21 00:00 | Trinidad & Tobago v USA | W | 2-1 |
| CONCACAF Nations League | 2023/11/17 02:00 | USA v Trinidad & Tobago | L | 3-0 |
| CONCACAF Nations League | 2023/10/18 01:00 | Curacao v Trinidad & Tobago | L | 5-3 |
| CONCACAF Nations League | 2023/10/14 01:00 | Trinidad & Tobago v Guatemala | W | 3-2 |
| CONCACAF Nations League | 2023/09/11 02:10 | El Salvador v Trinidad & Tobago | W | 2-3 |
| CONCACAF Nations League | 2023/09/07 22:00 | Trinidad & Tobago v Curacao | W | 1-0 |
| CONCACAF Gold Cup | 2023/07/02 23:00 | USA v Trinidad & Tobago | L | 6-0 |
| CONCACAF Gold Cup | 2023/06/28 23:30 | Jamaica v Trinidad & Tobago | L | 4-1 |
Away History
| CONCACAF Nations League | 2023/11/22 00:30 | Canada v Jamaica | W | 2-3 |
| CONCACAF Nations League | 2023/11/18 15:30 | Jamaica v Canada | L | 1-2 |
| International Match | 2023/11/12 00:00 | Guatemala v Jamaica | D | 0-0 |
| CONCACAF Nations League | 2023/10/16 00:00 | Haiti v Jamaica | W | 2-3 |
| CONCACAF Nations League | 2023/10/12 23:00 | Grenada v Jamaica | W | 1-4 |
| CONCACAF Nations League | 2023/09/13 00:05 | Jamaica v Haiti | D | 2-2 |
| CONCACAF Nations League | 2023/09/09 01:10 | Jamaica v Honduras | W | 1-0 |
| CONCACAF Gold Cup | 2023/07/13 02:00 | Jamaica v Mexico | L | 0-3 |