Anguilla national football team

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 3,000 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.

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 March 2008. In front of 22,670 spectators, Anguilla lost the second leg 4–0, thereby losing to El Salvador by an aggregate score of 16–0.

In the first round of the qualifiers for the 2014 World Cup in Brazil, Anguilla were again drawn to play the Dominican Republic, as they had eight years previously. On 8 July 2011, they lost 2–0 at the Estadio Panamericano in San Cristobal, and losing 4–0 in the same Dominican Republic stadium just two days later. This put the Dominican Republic through to the second round with the same 6–0 aggregate scoreline as their previous encounter.

In the first round of the qualifiers for the 2018 World Cup in Russia, Anguilla were drawn to play Nicaragua. On 23 March 2015, they lost the first leg 5–0 at the Dennis Martínez National Stadium in Managua, Nicaragua and, on 29 March 2015, were eliminated at Ronald Webster Park in The Valley in Anguilla with a 3–0 loss, to send Nicaragua through to the second round by a score of 8–0 on aggregate.

The pair of shutouts against Nicaragua in March 2015 extended Anguilla's scoreless run in World Cup qualification to eight matches, encompassing three World Cups over an eleven year period. The goals Anguilla scored in March 2000 against the Bahamas in each leg of their first World Cup qualifying appearance remain their only two goals, with 41 goals conceded, no wins, one draw and nine losses from their ten World Cup qualifying matches to date.[6]

The following players have been called up within the past 12 months.