From 1958 to 1962, Saint Christopher-Nevis-Anguilla formed a province of the West Indies Federation, electing two members to the House of Representatives and also having two senators, appointed by the Governor-General.

On 7 November 1970, a commission led by Hugh Wooding, former Chief Justice of Trinidad and Tobago, published report which unanimously refused both the idea of independent Anguilla and the return of the status of a British colony and recommended that the island should instead remain a part of Saint Christopher-Nevis-Anguilla.

[4] Foreign and Commonwealth Office Minister Joseph Godber stated in the House of Commons of the United Kingdom that his government will analyze the report in light of discussions with all interested parties and that no decision unacceptable to the people of Anguilla will be made.

[7] Sir Frederick Albert Phillips, the first governor of Saint Christopher-Nevis-Anguilla, wrote in 2013:[2] It is generally acknowledged that the federation failed on several counts.

At the 1978 Commonwealth Games in Edmonton, Alberta, Canada, the federation sent four competitors (two runners and two cyclists, all male), but failed to win a medal.