Head to Head
| CONCACAF Nations League | 2019/09/05 19:00 | US Virgin Islands v Cayman Islands | W | 0-2 |
Home History
| CONCACAF Nations League | 2019/10/15 23:30 | Cayman Islands v Saint Martin | W | 1-0 |
| CONCACAF Nations League | 2019/10/12 19:00 | Saint Martin v Cayman Islands | L | 3-0 |
| CONCACAF Nations League | 2019/09/08 23:30 | Cayman Islands v Barbados | W | 3-2 |
| CONCACAF Nations League | 2019/09/05 19:00 | US Virgin Islands v Cayman Islands | W | 0-2 |
| CONCACAF Nations League Qualifying | 2019/03/22 22:30 | Cayman Islands v Montserrat | L | 1-2 |
| CONCACAF Nations League Qualifying | 2018/11/18 01:00 | Cayman Islands v Saint Lucia | D | 0-0 |
| CONCACAF Nations League Qualifying | 2018/10/13 00:00 | Dominican Republic v Cayman Islands | D | 0-0 |
| CONCACAF Nations League Qualifying | 2018/09/10 00:00 | Jamaica v Cayman Islands | L | 4-0 |
Away History
| CONCACAF Nations League | 2019/10/15 21:00 | US Virgin Islands v Barbados | L | 0-4 |
| CONCACAF Nations League | 2019/10/13 00:00 | Barbados v US Virgin Islands | L | 1-0 |
| CONCACAF Nations League | 2019/09/08 19:00 | Saint Martin v US Virgin Islands | W | 1-2 |
| CONCACAF Nations League | 2019/09/05 19:00 | US Virgin Islands v Cayman Islands | L | 0-2 |
| CONCACAF Nations League Qualifying | 2019/03/22 22:00 | Anguilla v US Virgin Islands | W | 0-3 |
| 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 |
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