Richard O'Connor

2002 World Cup qualification

Anguilla entered the World Cup qualifiers for the first time for the 2002 World Cup in South Korea and Japan. 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.

2006 World Cup qualification

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.

2010 World Cup qualification

During the qualifiers for the 2010 World Cup in South Africa, Anguilla was drawn against El Salvador in the first round. 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. This time, Anguilla played their "home leg" at RFK Stadium in Washington, D.C. in the United States on 26…