List of Chief Ministers of Anguilla
| Incumbent | Tenure | Political Affiliation | ||
|---|---|---|---|---|
| Took Office | Left Office | |||
| Ronald Webster | 10 February 1976 | 1 February 1977 | People's Progressive Party (to 1977); Anguilla United Party | |
| Emile Gumbs | 1 February 1977 | May 1980 | Anguilla National Alliance | |
| Ronald Webster | May 1980 | 12 March 1984 | Anguilla United Party (to 1981); Anguilla National Alliance | |
| Emile Gumbs | 12 March 1984 | 16 March 1994 | Anguilla National Alliance | |
| Hubert Hughes | 16 March 1994 | 6 March 2000 | Anguilla United Party | |
| Osbourne Fleming | 6 March 2000 | 16 February 2010 | Anguilla United Front (Anguilla National Alliance & Anguilla Democratic Party) | |
| Hubert Hughes | 16 February 2010 | Present | Anguilla United Movement | |
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