Founded in 1881 as a boys' school, Caulfield Grammar began admitting girls exactly one hundred years later.

It has an outdoor education campus at Yarra Junction, and a student centre in Nanjing, China where the Year 9 internationalism programme is conducted.

[2] Joseph Henry Davies, who had served as a missionary in southern India, purchased the site for the school — it was adjacent to the Elsternwick railway station, and had been a small lolly shop[3] — for £25 on 16 April and employed his sister and two brothers as teachers.

To house the growing student body, the school then moved to a nearby small building, later destroyed in a fire in 1890.

[10][11] The current site, a property near Sir Frederick Sargood's Rippon Lea Estate on what is now Glen Eira Road, St Kilda East was purchased in 1909.

[26] The school established a computer network in 1997 with all students and staff having individual log in details, email accounts, and file space.

[28] The school's historic War Memorial Hall, opened by Sir Dallas Brooks, the Governor of Victoria, on 27 April 1958, had cost some £50,000 (approx.

[29][30] In the early morning of 7 November 2000, the "Cup Day" public holiday, a fierce fire broke out in the then-being-refurbished building (just two weeks away from completion); the roof collapsed, and the entire building was destroyed — only Alan Sumner's stained glass memorial windows escaped damage.

The Yarra Junction Campus today allows students to live in sustainable eco-cabins with rainwater tanks and solar power technology.

[45] Stephen Newton, Caulfield Grammar's principal from 1993 to 2011, was made an Officer of the Order of Australia in 2012, for "distinguished service to education in the independent schools sector, through executive roles with professional organisations and advisory bodies, and to the development of educational development opportunities with China," recognising his role in founding the Nanjing Campus.

The school awards scholarships for a range of fields, including academic excellence, theatre, music, art and sports.

After initially poor results the school introduced compulsory involvement in sporting teams in 1958 in an attempt to improve its performance.

In 2005, Australian jazz musician James Morrison performed with the "No Strings Attached" stage band at Monash University.

[67] A number of Caulfield Grammar alumni have made significant contributions in the fields of government, sports, music, business and academia among others.

Among those who have had involvement in politics, Peter Dowding (Western Australia) and Lindsay Thompson (Victoria), have served as state premiers.

Free-style swimmer Mack Horton has won multiple medals at the Olympic Games, World Championships and Commonwealth Games, including a gold medal in the 400m freestyle event at the 2016 Summer Olympics in Rio de Janeiro, Brazil.

John Clifford Valentine Behan, later second Warden of Trinity College at the University of Melbourne, became the first Victorian Rhodes Scholar after graduating as the Dux of Caulfield Grammar School in 1895.

[69] Fred Walker founded the company that first created and sold Vegemite, an Australian spread and cultural icon.

Cave and Harvey had been members of the school choir under the direction of Norman Kaye, who became a noted actor and musician after working at Caulfield Grammar as a music teacher and choirmaster.