Head to Head
| CONCACAF Nations League | 2019/10/16 00:00 | Anguilla v Puerto Rico | W | 2-3 |
Home History
| CONCACAF Nations League | 2019/11/17 01:00 | Guatemala v Puerto Rico | L | 5-0 |
| CONCACAF Nations League | 2019/10/16 00:00 | Anguilla v Puerto Rico | W | 2-3 |
| CONCACAF Nations League | 2019/09/11 01:00 | Puerto Rico v Guatemala | L | 0-5 |
| CONCACAF Nations League | 2019/09/11 01:00 | Puerto Rico v Guatemala | L | 0-5 |
| International Match | 2019/09/06 01:00 | Honduras v Puerto Rico | L | 4-0 |
| CONCACAF Nations League Qualifying | 2019/03/24 20:00 | Puerto Rico v Grenada | L | 0-2 |
| CONCACAF Nations League Qualifying | 2018/11/17 02:00 | Belize v Puerto Rico | L | 1-0 |
| CONCACAF Nations League Qualifying | 2018/09/10 00:00 | St. Kitts and Nevis v Puerto Rico | L | 1-0 |
Away History
| CONCACAF Nations League | 2019/10/16 00:00 | Anguilla v Puerto Rico | L | 2-3 |
| CONCACAF Nations League | 2019/10/13 00:00 | Anguilla v Guatemala | L | 0-5 |
| CONCACAF Nations League | 2019/09/06 02:00 | Guatemala v Anguilla | L | 10-0 |
| CONCACAF Nations League Qualifying | 2019/03/22 22:00 | Anguilla v US Virgin Islands | L | 0-3 |
| CONCACAF Nations League Qualifying | 2018/11/18 23:00 | Bahamas v Anguilla | D | 1-1 |
| CONCACAF Nations League Qualifying | 2018/10/14 23:00 | Nicaragua v Anguilla | L | 6-0 |
| Central America - World Cup Qualifying | 2015/03/29 21:00 | Anguilla v Nicaragua | L | 0-3 |
| Central America - World Cup Qualifying | 2015/03/24 00:00 | Nicaragua v Anguilla | L | 5-0 |