| Friendlies | 11/10/10 | Jamaica | - | Trinidad & Tobago | 1:0 | ||||
| Friendlies | 16/11/13 | Jamaica | - | Trinidad & Tobago | 0:1 | ||||
| Friendlies | 20/11/13 | Trinidad & Tobago | - | Jamaica | 2:0 | ||||
| Gold Cup QF | 19/11/14 | Jamaica | - | Trinidad & Tobago | 4:3 pso |  |
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| Friendlies | 11/03/23 | Jamaica | - | Trinidad & Tobago | 0:1 | ||||
| Friendlies | 15/03/23 | Jamaica | - | Trinidad & Tobago | 0:0 | ||||
| Gold Cup | 29/06/23 | Jamaica | - | Trinidad & Tobago | 4:1 | ||||
| Friendlies | 07/02/25 | Jamaica | - | Trinidad & Tobago | 1:0 |
Trinidad & Tobago