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Turks/Caicos Islands which comes under Canadian control if I'm not mistaken
Not really, but they do have some history...
From
Wikipedia:
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In 1917, Canadian Prime Minister Robert Borden suggested that the Turks and Caicos join Canada, but this suggestion was shot down by British prime minister David Lloyd George. The islands remained a dependency of Jamaica until 1959
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In 1974, Canadian New Democratic Party leader Max Saltsman tried to use his Private Member's Bill to create legislation to annex the islands to Canada, but it didn't pass in the Canadian House of Commons.
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In 1979, independence was agreed upon in principle for 1982, but a change in government caused a policy reversal, and they instead approached the Canadian government to discuss a possible union, but at the time the Canadian Government was embroiled in a debate over free trade with the U.S., and little attention was paid to the suggestion.