Headmasters
Reverend F T Perkins 1918 - 1932
The buildings along the drive took shape during Reverend Perkins' time. The main classroom block was built between 1919 and 1921, and was named the Perkins Building in 1946. Harvey House was built in 1919 and was renamed Street House in 1979. The Health Centre was built in 1927. The Headmaster's House was built in circa 1880 and enlarged in 1927. Sporting facilities included the Sports Oval which was built in 1918 and renamed the Hordern Oval in 1948. Rose Bay Playing Fields were opened in 1929 and were renamed Dangar Playing Fields in 1948. The gymnasium was built in 1925. The first three Houses were formed in 1930 and were named Chelmsford, Rawson and Strickland in 1931. Features of the School calendar at that time included sports days from 1918, swimming carnivals from 1922, and Speech Day and Foundation Day. Fundraising also commenced, with the first fair being held in 1922.
Brigadier I Mackay 1933 - 1939
1934 saw the enrolment age lowered to five years and the formal separation of the Junior School from the Senior School. A scout troop was formed in 1933. The appointment of the first Chaplain and the consecration of a temporary Chapel occurred in 1934. Brigadier Mackay emphasised greater discipline and rigour in academic subjects, and at the same time introduced more practical subjects, such as metalwork, wool classing and bookkeeping.
B Hone 1940 - 1950
In 1941 the House system was restructured to incorporate academic, pastoral and administrative matters, and this system became the centre of School life. Davidson House was established. A new holistic approach to the care and education of each student became the focus of the Cranbrook education. In 1941 the Report Book was introduced. In 1944 two preschools were established at St Mark's, Darling Point, and St Michael's, Vaucluse. The School Committee, now known as the Student Representative Council, was restructured as a student-centred body. Fundraising began for the War Memorial Hall in 1946. The Perkins Building featured a senior library and a physics laboratory. Rona was purchased in 1947. This facility provided extra boarding from 1947 to 1950.
G Hewan 1951 - 1963
Further facilities were added during Mr Hewan's time. The War Memorial Hall was built in 1953. Dickins House was built at the Preparatory School in Rose Bay in 1959 and the Senior School Science Building was built in 1962 to be renamed the Bishop Building in 1985. Leura was purchased in 1956 and renamed Street House. This facility provided additional boarding. Three new Houses were founded; Northcott and Street in 1957, and Wakehurst in 1960. The arts developed during the 1950s; art under the leadership of Justin O'Brien, and music under the leadership of Gordon Day and Charles Colman.
M Bishop 1963 - 1985
Cotway was purchased in 1964 and became the Junior Boarding House, and the new boat shed at Rose Bay was built in 1965. New Senior School facilities included the Mansfield Building built in 1968 and the Senior School Building including the swimming pool and gymnasium built during the years 1976 to 1981. In 1967 the first Higher School Certificate examinations were held. Japanese and soccer were introduced in 1966, and hockey was introduced in 1967. In 1975 Cranbrook in the Field (CITF) was extended from its origins as Outward Bound, which had been introduced in 1968. Three new day boy Houses were established, Woodward in 1969, Hone in 1970 and Cutler in 1980. 1982 saw the inauguration of The Cranbrook Chronicle.
Dr B N Carter 1985 - 2000
In 1985 the first Valedictory Dinner was held for Year 12 and the new School blazer was introduced to replace grey suits. Additional facilities opened included the Rowland Building in 1986 and the Furber Building (Junior School) in 1992. The Perkins Building became the home of music in 1992 and the Carter Building opened in 2000. 1987 saw the introduction of work experience. Perkins House was established in 1994.
J J S Madin 2001 - present
Cranbrook acquired the Rose Bay Bowling Club next to the Dangar Playing Fields. Construction of new grandstands and clubhouses at the Hordern Oval and Dangar Playing Fields began, and renovation of the Cranbrook building administration offices took place in 2003. The Senior School administration facility, including a new staff common room known as the Felton Room, opened in 2004. Renovations to various faculty offices, the upgrading of Senior School classrooms, completion of a new Junior School ICT and robotics laboratory, and the renovation of the Rotunda occurred in 2005.