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Sydney Boys High School has produced numerous prominent alumni, referred to as "Old Boys". Many graduates are active in alumni organisations, such as the Sydney High School Old Boys Union (OBU), the High Club, and High Rugby Friends. Scott Morrison, Prime Minister of Australia (2018–2022), is an alumnus of Sydney Boys High School.
In September 1883 Joseph Coates successfully applied for the headmastership of the soon to be established Sydney Boys' High School and Waterhouse as head of Maitland High School. Sydney High opened in October 1883 and as Coates could not leave Newington until the end of the year, John Waterhouse was appointed to open the school. His letter of ...
The NSW AAGPS (Athletic Association of the Great Public Schools) Athletics is one of the premier Athletics events in Australia. It is an annual event competed in between 9 member teams that include Saint Ignatius Riverview, St Joseph's Hunters Hill, Sydney Grammar, Sydney Boys High, Newington College, Scots College, The King's School, Sydney Church Of England (Shore), and The Armidale School.
Hon. Lionel Murphy – Justice of the High Court of Australia (1975–86), 22nd Attorney-General of Australia (1972–75), Federal Senator (1961–72) Hon. Albert Piddington – Justice of the High Court of Australia (teacher at Sydney Boys High School) [12] Hon. Nye Perram – current Justice of the Federal Court of Australia (2008–present)
The official rugby union competition commenced in 1892. In 2009 after 103 years playing in the 1st XV competition Sydney Boys High School decided to withdraw itself from AAGPS Rugby.
The Old Falconians Union is the alumni body of the school. The name "Old Falconians" is derived from Falcon Street which is the address of the school. All pupils who once attended the school are considered a part of the union, even if they were only on the roll for a short amount of time.
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As of 2021, all nine of the GPS schools, Sydney Grammar School, The King's School, Newington College, Sydney Boys High School, The Scots College, St. Joseph's College, Saint Ignatius' College, The Armidale School and Shore School, send their eights to the Head of the River.