Anguilla entered in the Caribbean qualifiers for the 2010 Gold Cup, held in Mexico during 28 October–8 November 2010. The team was drawn along with Barbados and Grenada. The first game (as away team) was in Barbados National Stadium and finished with an 0–3 loss to Barbados. Again in Barbados National Stadium, Anguilla faced Grenada, and the result was a 2–0 victory. Despite this result, Anguilla didn't qualify to the next stage because the only place from Group E was occupied by Barbados, who won both of its matches. With this result, Anguilla was also eliminated from the 2011 World Cup, celebrated in Germany.