Head to Head
| CONCACAF Nations League | 2022/06/03 20:00 | British Virgin Islands v Cayman Islands | D | 1-1 |
Home History
| CONCACAF Nations League | 2022/06/03 20:00 | British Virgin Islands v Cayman Islands | D | 1-1 |
| Central America - World Cup Qualifying | 2021/06/09 00:00 | Bermuda v Cayman Islands | D | 1-1 |
| Central America - World Cup Qualifying | 2021/06/02 22:00 | Cayman Islands v Aruba | L | 1-3 |
| Central America - World Cup Qualifying | 2021/03/29 22:00 | Cayman Islands v Canada | L | 0-11 |
| Central America - World Cup Qualifying | 2021/03/24 22:00 | Suriname v Cayman Islands | L | 3-0 |
| CONCACAF Nations League | 2019/11/20 00:00 | Barbados v Cayman Islands | L | 3-0 |
| CONCACAF Nations League | 2019/11/17 00:30 | Cayman Islands v US Virgin Islands | W | 1-0 |
| CONCACAF Nations League | 2019/10/15 23:30 | Cayman Islands v Saint Martin | W | 1-0 |
Away History
| CONCACAF Nations League | 2022/06/03 20:00 | British Virgin Islands v Cayman Islands | D | 1-1 |
| Central America - World Cup Qualifying | 2021/06/05 21:00 | British Virgin Islands v Curacao | L | 0-8 |
| Central America - World Cup Qualifying | 2021/06/02 21:30 | Cuba v British Virgin Islands | L | 5-0 |
| Central America - World Cup Qualifying | 2021/03/30 22:00 | St. Vincent/Grenadines v British Virgin Islands | L | 3-0 |
| Central America - World Cup Qualifying | 2021/03/27 22:00 | British Virgin Islands v Guatemala | L | 0-3 |
| CONCACAF Nations League | 2019/11/15 00:00 | Bahamas v British Virgin Islands | L | 3-0 |
| CONCACAF Nations League | 2019/10/13 19:00 | British Virgin Islands v Bonaire | L | 3-4 |
| CONCACAF Nations League | 2019/10/10 23:00 | British Virgin Islands v Bahamas | L | 0-4 |