Home History
| 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 |
| 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 |
Away History
| Central America - World Cup Qualifying | 2021/03/26 00:00 | Canada v Bermuda | W | 5-1 |
| International Match | 2020/01/16 00:00 | Canada v Iceland | L | 0-1 |
| International Match | 2020/01/11 00:30 | Barbados v Canada | W | 1-4 |
| International Match | 2020/01/08 00:30 | Canada v Barbados | W | 4-1 |
| CONCACAF Nations League | 2019/11/16 00:00 | USA v Canada | L | 4-1 |
| CONCACAF Nations League | 2019/10/15 23:30 | Canada v USA | W | 2-0 |
| CONCACAF Nations League | 2019/09/10 23:15 | Cuba v Canada | W | 0-1 |
| CONCACAF Nations League | 2019/09/08 00:00 | Canada v Cuba | W | 6-0 |