In front of a Bahamian crowd of just 330, the second leg was played at the Thomas Robinson Stadium in Nassau on 19 March 2000, with Anguilla losing 2–1, and thereby eliminated by an aggregate scoreline of 5–2.

The first leg was played to a goalless draw at the Estadio Olímpico Juan Pablo Duarte in Santo Domingo on 19 March 2004.

On 6 February 2008, they lost 12–0 at the Estadio Cuscatlán in San Salvador, where striker Rudis Corrales scored five times and Ronald Cerritos three.

In the first round of the qualifiers for the 2022 World Cup in Qatar, Anguilla were drawn into group D with Dominica, Barbados, Dominican Republic, and Panama, whom they’d each play once.

On 31 March 2021, they faced Barbados at Estadio Olímpico Félix Sánchez in Santo Domingo, Anguilla lost to a late 1–0 goal by Emile Saimovici.

At the commencement of 2026 FIFA World Cup qualification, Anguilla advanced beyond the first round of qualifying for the first time in their history after beating Turks and Caicos Islands 1–1 on aggregate after penalties.

Win Draw Loss Fixture The following players were called up for the 2024–25 CONCACAF Nations League C matches against Belize and Turks and Caicos on 9 and 12 October 2024.