The Anguilla national football team is the national team of Anguilla, a British Overseas Territory in the Caribbean, and is controlled by the Anguilla Football Association. It is affiliated to the Caribbean Football Union of CONCACAF. Along with the teams from the Bahamas, Tonga, Bhutan, Eritrea, San Marino, and Somalia, they are consistently one of the lowest ranked teams in the world in the FIFA rankings.
As of 12 August 2021, they rank 210th in the FIFA rankings, placing in last of all teams.
In the first round of the qualifiers, Anguilla were drawn against the Bahamas. On 5 March 2000, Anguilla hosted the first leg in front of 250 people at Webster Park in The Valley, losing by a scoreline of 3–1. 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.
During the qualifiers for the 2006 World Cup in Germany, Anguilla faced the Dominican Republic in the first round. The first leg was played to a goalless draw at the Estadio Olímpico Juan Pablo Duarte in Santo Domingo on 19 March 2004. Newly introduced FIFA stadium requirements forced Anguilla to play their “home” leg at the same Dominican Republic stadium two days later, with the Dominican Republic winning the second leg and thus the first round by a scoreline of 6–0.