Home History
| 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 |
| Central America - World Cup Qualifying | 2015/03/29 21:00 | Anguilla v Nicaragua | L | 0-3 |
| Central America - World Cup Qualifying | 2015/03/24 00:00 | Nicaragua v Anguilla | L | 5-0 |
| CFU Caribbean Cup | 2014/09/07 21:00 | Anguilla v Dominican Republic | L | 0-10 |
| CFU Caribbean Cup | 2014/09/05 21:00 | St. Vincent/Grenadines v Anguilla | L | 4-0 |
| CFU Caribbean Cup | 2014/09/03 23:00 | Antigua & Barbuda v Anguilla | L | 6-0 |
Away History
| CONCACAF Nations League Qualifying | 2018/11/18 23:00 | Barbados v US Virgin Islands | L | 3-0 |
| Central America - World Cup Qualifying | 2015/03/26 19:30 | US Virgin Islands v Barbados | L | 0-4 |
| Central America - World Cup Qualifying | 2015/03/22 23:00 | Barbados v US Virgin Islands | W | 0-1 |
| CFU Caribbean Cup | 2014/06/01 23:00 | US Virgin Islands v Bonaire | L | 1-2 |
| CFU Caribbean Cup | 2014/05/30 23:00 | Montserrat v US Virgin Islands | L | 1-0 |