Home History
| Central America - World Cup Qualifying | 2021/03/26 00:00 | Panama v Barbados | L | 1-0 |
| International Match | 2020/01/11 00:30 | Barbados v Canada | L | 1-4 |
| International Match | 2020/01/08 00:30 | Canada v Barbados | L | 4-1 |
| CONCACAF Nations League | 2019/11/20 00:00 | Barbados v Cayman Islands | W | 3-0 |
| CONCACAF Nations League | 2019/11/16 20:00 | Saint Martin v Barbados | L | 1-0 |
| CONCACAF Nations League | 2019/10/15 21:00 | US Virgin Islands v Barbados | W | 0-4 |
| CONCACAF Nations League | 2019/10/13 00:00 | Barbados v US Virgin Islands | W | 1-0 |
| CONCACAF Nations League | 2019/09/08 23:30 | Cayman Islands v Barbados | L | 3-2 |
Away History
| Central America - World Cup Qualifying | 2021/03/27 22:00 | Anguilla v Dominican Republic | L | 0-6 |
| CONCACAF Nations League | 2019/11/19 22:00 | Puerto Rico v Anguilla | L | 3-0 |
| 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 |