Head to Head
| CONCACAF Nations League | 2024/10/15 01:00 | Trinidad & Tobago v Cuba | L | 3-1 |
| CONCACAF Nations League | 2024/10/10 20:00 | Cuba v Trinidad & Tobago | D | 2-2 |
| CONCACAF Gold Cup | 2015/07/12 22:30 | Trinidad & Tobago v Cuba | L | 2-0 |
Home History
| CONCACAF Nations League | 2024/11/18 19:00 | Cuba v St. Kitts and Nevis | W | 4-0 |
| CONCACAF Nations League | 2024/11/14 23:00 | St. Kitts and Nevis v Cuba | L | 2-1 |
| CONCACAF Nations League | 2024/10/15 01:00 | Trinidad & Tobago v Cuba | L | 3-1 |
| CONCACAF Nations League | 2024/10/10 20:00 | Cuba v Trinidad & Tobago | D | 2-2 |
| CONCACAF Nations League | 2024/09/10 20:00 | Cuba v Nicaragua | D | 1-1 |
| CONCACAF Nations League | 2024/09/07 00:00 | Jamaica v Cuba | D | 0-0 |
| North & Central America - World Cup Qualifying | 2024/06/07 00:30 | Honduras v Cuba | L | 3-1 |
| International Match | 2024/03/27 01:00 | Nicaragua v Cuba | W | 0-1 |
Away History
| 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 |
| 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 |