To date, only two women, Idalia Gumbs and Abena Lake-Hodge, have sat as elected members of the House of Assembly. Idalia Gumbs was the first woman to become a member of Anguilla’s legislature with her appointment, in 1972, as a Nominated Member of the Anguilla Council on the recommendation of Ronald Webster, the island’s political leader. Four years later (in 1976) she and Albena Lake-Hodge (Teacher Albena), who were members of Webster’s People Progressive Party (PPP), won seats in the Legislative Assembly. Teacher Albena was appointed Minister of Social Services.

Four women unsuccessfully contested the 1989 general election. They were Ophelia Richardson, Orealia Kelly, Lolita Davis-Ifill and Omah Richardson.

In 1999, after a 10-year break, Anguilla’s women returned to the political platform with Barbara Webster contesting the Island Harbour seat and Blondell Rodgiers The Valley South seat..  As in 1989, neither candidate was successful.  Nonetheless, in every general election thereafter, female candidates contested for seats.

Four women contested the 2000 general election: Barbara Webster, Margaret Augustus, Joyce Kentish and Rhona Richardson. Three contested the 2005 election: Barbara Webster, Anne Edwards and Rhona Richardson; and Palmavon Webster and Cora Richardson-Hodge contested the 2010 election.  All were unsuccessful in their bids.

On 26 February 2010, Barbara Webster-Bourne became the first woman to be elected to the position of Speaker of the House of Assembly following the victory of the Anguilla United Movement in the 15 February 2015 election.

Four female candidates - three lawyers, Palmavon Webster, Cora Richardson-Hodge and Kristy Richardson-Harrigan, and one senior retired public servant, Evalie Bradley contestested the 2015 election. Webster, Richardson-Hodge, and Bradley were all victorious in their specific districts, representing the first return of elected women representatives in 30 years.