Head to Head
| CONCACAF Nations League | 2023/09/07 23:00 | US Virgin Islands v Cayman Islands | D | 2-2 |
| CONCACAF Nations League | 2019/11/17 00:30 | Cayman Islands v US Virgin Islands | W | 1-0 |
| CONCACAF Nations League | 2019/09/05 19:00 | US Virgin Islands v Cayman Islands | W | 0-2 |
Home History
| CONCACAF Nations League | 2023/09/11 20:30 | Cayman Islands v Aruba | L | 1-2 |
| CONCACAF Nations League | 2023/09/07 23:00 | US Virgin Islands v Cayman Islands | D | 2-2 |
| CONCACAF Nations League | 2023/03/26 22:00 | Puerto Rico v Cayman Islands | L | 5-1 |
| CONCACAF Nations League | 2022/06/09 22:00 | Cayman Islands v Puerto Rico | L | 0-3 |
| CONCACAF Nations League | 2022/06/06 22:00 | Cayman Islands v British Virgin Islands | D | 1-1 |
| CONCACAF Nations League | 2022/06/03 20:00 | British Virgin Islands v Cayman Islands | D | 1-1 |
| Nord- & Mittelamerika - WM-Qualifikation | 2021/06/09 00:00 | Bermuda v Cayman Islands | D | 1-1 |
| Nord- & Mittelamerika - WM-Qualifikation | 2021/06/02 22:00 | Cayman Islands v Aruba | L | 1-3 |
Away History
| CONCACAF Nations League | 2023/10/14 19:00 | Aruba v US Virgin Islands | L | 3-1 |
| CONCACAF Nations League | 2023/09/07 23:00 | US Virgin Islands v Cayman Islands | D | 2-2 |
| CONCACAF Nations League | 2023/03/28 23:00 | US Virgin Islands v Sint Maarten | L | 1-2 |
| CONCACAF Nations League | 2023/03/25 19:30 | Turks & Caicos Islands v US Virgin Islands | L | 1-0 |
| CONCACAF Nations League | 2022/06/14 20:00 | Bonaire v US Virgin Islands | L | 2-0 |
| CONCACAF Nations League | 2022/06/11 20:00 | US Virgin Islands v Bonaire | L | 0-2 |
| CONCACAF Nations League | 2022/06/06 20:00 | US Virgin Islands v Turks & Caicos Islands | W | 3-2 |
| CONCACAF Nations League | 2022/06/03 20:30 | Sint Maarten v US Virgin Islands | D | 1-1 |