Head to Head
| CONCACAF Nations League | 2019/11/19 22:00 | Puerto Rico v Anguilla | W | 3-0 |
| CONCACAF Nations League | 2019/10/16 00:00 | Anguilla v Puerto Rico | W | 2-3 |
Home History
| North & Central America - World Cup Qualifying | 2024/06/07 02:30 | El Salvador v Puerto Rico | D | 0-0 |
| International Match | 2024/03/22 01:30 | Belize v Puerto Rico | D | 1-1 |
| CONCACAF Nations League | 2023/11/22 00:00 | Puerto Rico v Bahamas | W | 6-1 |
| CONCACAF Nations League | 2023/11/18 19:00 | Antigua & Barbuda v Puerto Rico | W | 2-3 |
| CONCACAF Nations League | 2023/10/17 20:00 | Guyana v Puerto Rico | L | 3-1 |
| CONCACAF Nations League | 2023/10/14 19:00 | Puerto Rico v Guyana | L | 1-3 |
| CONCACAF Nations League | 2023/09/12 23:05 | Puerto Rico v Antigua & Barbuda | W | 5-0 |
| CONCACAF Nations League | 2023/09/09 22:00 | Bahamas v Puerto Rico | W | 1-6 |
Away History
| North & Central America - World Cup Qualifying | 2024/06/08 19:30 | Anguilla v Suriname | L | 0-4 |
| Central America - World Cup Qualifying | 2024/03/26 23:00 | Turks & Caicos Islands v Anguilla | W | 4-5 |
| Central America - World Cup Qualifying | 2024/03/22 19:00 | Anguilla v Turks & Caicos Islands | D | 0-0 |
| CONCACAF Nations League | 2023/11/18 19:00 | Anguilla v Bonaire | L | 0-3 |
| 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 |