Head to Head
| CONCACAF Nations League | 2023/10/12 23:00 | Bonaire v Anguilla | L | 2-0 |
Home History
| CONCACAF Nations League | 2023/10/16 20:00 | Saint Martin v Anguilla | L | 8-0 |
| CONCACAF Nations League | 2023/10/12 23:00 | Bonaire v Anguilla | L | 2-0 |
| CONCACAF Nations League | 2023/09/07 20:00 | Anguilla v Saint Martin | L | 0-6 |
| CONCACAF Nations League | 2023/03/24 19:00 | Anguilla v Saint Lucia | L | 1-2 |
| CONCACAF Nations League | 2022/06/12 22:00 | Saint Lucia v Anguilla | L | 2-0 |
| CONCACAF Nations League | 2022/06/05 19:00 | Dominica v Anguilla | D | 1-1 |
| CONCACAF Nations League | 2022/06/02 20:00 | Anguilla v Dominica | D | 0-0 |
| Central America - World Cup Qualifying | 2021/06/06 00:00 | Panama v Anguilla | L | 13-0 |
Away History
| CONCACAF Nations League | 2023/10/12 23:00 | Bonaire v Anguilla | W | 2-0 |
| CONCACAF Nations League | 2023/09/11 23:00 | Saint Martin v Bonaire | L | 2-1 |
| CONCACAF Nations League | 2023/03/28 23:00 | Bonaire v Turks & Caicos Islands | L | 1-2 |
| CONCACAF Nations League | 2023/03/25 20:00 | Sint Maarten v Bonaire | L | 6-1 |
| CONCACAF Nations League | 2022/06/14 20:00 | Bonaire v US Virgin Islands | W | 2-0 |
| CONCACAF Nations League | 2022/06/11 20:00 | US Virgin Islands v Bonaire | W | 0-2 |
| CONCACAF Nations League | 2022/06/06 20:00 | Bonaire v Sint Maarten | D | 2-2 |
| CONCACAF Nations League | 2022/06/03 20:30 | Turks & Caicos Islands v Bonaire | W | 1-4 |
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