Knox Grammar School was established on Sydney's North Shore in 1924, by the Presbyterian Church. The school was named after John Knox,[12] the 16th century Scottish reformer, who planned a network of schools in every church parish.Knox opened as a Presbyterian Boys' School after founding members John Gilmore, William McIlrath, Robert Gillespie and Andrew Reid purchased the original property, 'Earlston', as the first school building.Now the Gillespie Heritage House, 'Earlston' was previously owned by Sir Charles Mackellar, was designed by architects Spain & Cosh, and built in 1908 for W. Moses Esq., Warrawee.
The school was officially opened by the Hon. Sir George Fuller KCMG, Premier of New South Wales, on 5 February 1924. Under the founding headmaster Neil MacNeil, a Rhodes Scholar, Knox grew rapidly and survived theGreat Depression. Student numbers rose from 28 in 1924 to over 300 in 1939.
In 1939, Dr William Bryden FRSE (1904-1992)took over the role of headmaster. As World War II broke out, around 370 Old Knox Grammarians served in the armed forces. 53 of them lost their lives and are now commemorated in the John Williams Memorial Hall, the School Chapel, the Old Students' War Memorial, and the original Science Building. The school's Pipe Band was established during Bryden's period as headmaster.
Dr John Mill Couper, a Scot, became headmaster in 1953. Couper focused on broadening the School's education, with attention to music and art, however, problems culminated in Couper's departure from a divided Knox in 1955.
Dr T Ross McKenzie, former head of Brisbane Boys' College, replaced Couper. The school's fifth headmaster, Dr Ian Paterson, initiated further developments including a substantial building program.During this period three teachers sexually abused students; these teachers were later convicted and it has been alleged that other teachers abused students. In 2015 Paterson told the Royal Commission into Institutional Responses to Child Sexual Abuse that he had failed to protect students from abuse.
In 1999, Peter Crawley, former Head of Trinity Grammar School in Melbourne, became Knox's sixth headmaster.