Home History
| Landskampe | 2019/10/14 22:00 | Venezuela v Trinidad & Tobago | L | 2-0 |
| CONCACAF Nations League | 2019/10/10 23:15 | Trinidad & Tobago v Honduras | L | 0-2 |
| Landskampe | 2019/10/03 02:00 | Mexico v Trinidad & Tobago | L | 2-0 |
| CONCACAF Nations League | 2019/09/10 01:00 | Trinidad & Tobago v Martinique | D | 2-2 |
| CONCACAF Nations League | 2019/09/06 22:00 | Martinique v Trinidad & Tobago | D | 1-1 |
| CONCACAF Gold Cup | 2019/06/26 22:30 | Trinidad & Tobago v Guyana | D | 1-1 |
| CONCACAF Gold Cup | 2019/06/23 00:00 | USA v Trinidad & Tobago | L | 6-0 |
| CONCACAF Gold Cup | 2019/06/18 23:30 | Panama v Trinidad & Tobago | L | 2-0 |
Away History
| CONCACAF Nations League | 2019/10/16 00:00 | Anguilla v Puerto Rico | L | 2-3 |
| CONCACAF Nations League | 2019/10/13 00:00 | Anguilla v Guatemala | L | 0-5 |
| CONCACAF Nations League | 2019/09/06 02:00 | Guatemala v Anguilla | L | 10-0 |
| CONCACAF Nations League Qualifying | 2019/03/22 22:00 | Anguilla v US Virgin Islands | L | 0-3 |
| CONCACAF Nations League Qualifying | 2018/11/18 23:00 | Bahamas v Anguilla | D | 1-1 |
| CONCACAF Nations League Qualifying | 2018/10/14 23:00 | Nicaragua v Anguilla | L | 6-0 |
| Nord- og Mellemamerika - VM - Kvalifikation | 2015/03/29 21:00 | Anguilla v Nicaragua | L | 0-3 |
| Nord- og Mellemamerika - VM - Kvalifikation | 2015/03/24 00:00 | Nicaragua v Anguilla | L | 5-0 |