| Gold Cup QF | 26/11/10 | Trinidad & Tobago | - | Cuba | 0:2 | ||||
| Gold Cup QF | 16/11/14 | Cuba | - | Trinidad & Tobago | 0:0 | ||||
| Gold Cup | 12/07/15 | Trinidad & Tobago | - | Cuba | 2:0 | ||||
| CONCACAF NLA | 10/10/24 | Cuba | - | Trinidad & Tobago | 2:2 |  |
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| CONCACAF NLA | 15/10/24 | Trinidad & Tobago | - | Cuba | 3:1 | |
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| Gold Cup QF | 21/03/25 | Cuba | - | Trinidad & Tobago | 1:2 | ||||
| Gold Cup QF | 25/03/25 | Trinidad & Tobago | - | Cuba | 4:0 |
Trinidad & Tobago