Home History
| 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 Qualifying | 2018/11/17 01:00 | Aruba v Montserrat | W | 0-2 |
| Central America - World Cup Qualifying | 2015/03/31 22:30 | Montserrat v Curacao | D | 2-2 |
| Central America - World Cup Qualifying | 2015/03/28 00:00 | Curacao v Montserrat | L | 2-1 |
| CFU Caribbean Cup | 2014/06/03 23:00 | Montserrat v Bonaire | D | 0-0 |
| CFU Caribbean Cup | 2014/05/30 23:00 | Montserrat v US Virgin Islands | W | 1-0 |