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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.
The NSW AAGPS (Athletic Association of the Great Public Schools of New South Wales) is a school basketball competition played in Australia.It is an annual, 14 round competition played between 8 Sydney member teams that include Saint Ignatius Riverview, St Joseph's Hunters Hill, Sydney Grammar, Sydney Boys High, Newington College, Scots College, The Kings school and Sydney Church Of England ...
The official football competition commenced in 1988 . 1st Grade The Wanderers' Cup for AAGPS Soccer presented in 1988 by The King's School to mark the first school-based game of Soccer in Australia between The King's School and The Gentlemen Wanderers played in Parramatta on 14 August 1880.
In 2009 after 103 years playing in the 1st XV competition Sydney Boys High School decided to withdraw itself from AAGPS Rugby. After a two-year absence High returned in 2011 with their 1st XV in the 2nd XV competition.
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.
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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)
Outterside, a number 8, was born in Sydney and played two international rugby matches for Australia. Away from football, Outterside was also a successful teacher and school administrator, rising to become Headmaster of Sydney Boys High School. [2] In 1990 he was appointed an Officer of the Order of Australia (AO) for service to education. [3]