Home History
| 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 |
| Central America - World Cup Qualifying | 2015/03/30 00:00 | Cayman Islands v Belize | D | 1-1 |
| Central America - World Cup Qualifying | 2015/03/26 02:00 | Belize v Cayman Islands | D | 0-0 |
Away History
| CONCACAF Nations League | 2019/09/05 22:00 | Barbados v Saint Martin | W | 4-0 |
| CONCACAF Nations League Qualifying | 2019/03/25 00:00 | Barbados v Nicaragua | L | 0-1 |
| CONCACAF Nations League Qualifying | 2018/11/18 23:00 | Barbados v US Virgin Islands | W | 3-0 |
| CONCACAF Nations League Qualifying | 2018/10/14 02:00 | El Salvador v Barbados | L | 3-0 |
| CONCACAF Nations League Qualifying | 2018/09/06 23:02 | Guyana v Barbados | D | 2-2 |
| International Match | 2018/08/29 23:59 | Barbados v Cuba | L | 0-2 |
| International Match | 2018/08/26 23:02 | Barbados v Cuba | D | 0-0 |
| International Match | 2018/08/21 00:06 | Barbados v Jamaica | D | 2-2 |