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.[4]
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.
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.
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]
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