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The New South Wales government of the day established a model school at the old military barracks on Observatory Hill; this school was not only intended to educate boys and girls, but also to serve as a model for other schools in the colony. The school's name is derived from the name of a street which ran into the grounds of the hospital and became part of the playground during its reconstruction.

In 1916, the school split into Fort Street Boys' High and Fort Street Girls' High, with the former moving to the school's present site. The Girls' school remained at Observatory Hill until 1975, when the two schools were amalgamated to form the current coeducational school at Petersham.

The school's graduates include:

• Sir Edmund Barton, the first Prime Minister of Australia
• Neville Wran , former Premier of New South Wales
• H V Evatt, jurist and politician
• Michael Kirby, currently serving Justice of the High Court of Australia
• Sir Garfield Barwick, former Justice of the High Court
• Douglas Mawson, Antarctic explorer
• Dr John Yu, Australian of the Year 19961996 was a leap year starting on Monday (see link for calendar), and was designated the International Year for the Eradication of Poverty''. Events January January 5 Hamas operative Yahya Ayyash is killed by an Israeli-planted booby-trapped cell phone Jan
• Margaret PrestonMargret Preston ( 1875- 1963) was a widely known Australian artist, she was very influential during the 1920's 1940's for her works as a printmaker. Born Margaret Rose Mcpherson in 1875, Margaret decided early in life to become an artist. In 1888 she trai, artist and teacher of art
• Mary KostakidisMary Kostakidis is an Australian newsreader for the Special Broadcasting Service (SBS). She hosts the main SBS World News at 6. 30PM Weekdays., SBSSee: Special Broadcasting Service Australian government-funded Radio and TV network Special Boat Service a special forces unit of the British Royal Marines. SBS Broadcasting Group (originally Scandinavian, now also operating in various other European coun newsreader and a member of founding management team

Fort Street High School, being selective, draws students from across metropolitan Sydney and across the multicultural spectrum. The school's motto is "Faber est quisque fortunae" ("Every man is the maker of his own fortune").