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Margaret Ann Montgomery Bailey (9 June 1879 – 5 June 1955) was the headmistress of Ascham School in Edgecliff, New South Wales. During her 30 years as headmistress, her educational philosophy raised Ascham School to prosperity and prominence across Australia. The school totaled over 400 students at her retirement in 1947. She was an educator, world traveler, and women's activist.

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