- The Reverend Frederick Perkins -
1918 - 1929

Cranbrook opened its doors on 22 July 1918 and the first classes were held the following day. Under the auspices of the Reverend Frederick Perkins, the first Headmaster, the School Motto and crest were created, the first School Council was established and the School Song was adopted.

  • <p><span style="font-size:15.5px;">Reverend FT Perkins was appointed as Cranbrook's first Headmaster in February 1918, five months before the School's commencement.</span></p>
  • <p><span style="font-size:15.5px;">On opening day there were 64 boys, of whom 26 were boarders. <a href="https://cranbrookcentenary.com.au/stories/96?tid=1"><strong>Learn more about Reverend F T Perkins</strong></a>.</span></p>
- Brigadier Iven Mackay -
1930 - 1939

In the wake of World War 1, Headmaster Brigadier Iven Mackay formed the Preparatory School and formally separated the Junior School from the Senior School; in addition, three more Houses were founded and the Chapel was consecrated.

  • <p><span style="font-size:15.5px;">In 1933, Mackay became the second Headmaster until the end of 1939. At the start of his headmastership there were 212 boys, of whom 186 were day boys and 26 were boarders.</span></p>
- Sir Brian Hone -
1940 - 1949

Brian Hone established St Mark's and St Michael's Pre-schools, Harvey House was re-opened as the Junior School and air raid shelters were built on the banks of the School Oval, which was re-named Hordern Oval.

  • <p><span style="font-size:15.5px;">Brian Hone was Headmaster at Cranbrook from August 1940 until 1951. In 1940, due to the war years, there were only 190 boys, of whom 140 were day boys and 50 were boarders. <a href="https://cranbrookcentenary.com.au/stories?tid=3"><strong>Learn more about Brian Hone</strong></a>.</span></p>
  • <p><span style="font-size:15.5px;"><a href="https://cranbrookcentenary.com.au/stories/167?tid=3"><strong>Read about the Joklik family</strong></a>.</span></p>
- Mr Gethyn Hewen -
1950 - 1959

The new Headmaster, Mr Gethyn Hewen, opened the War Memorial Hall, the Rose Bay Boatshed and the Prep School ("Dickins House") in Kent Road, Rose Bay. Northcott and Street Houses were established in 1957.

  • <p><span style="font-size:15.5px;">Mr Hewan was offered the position of Headmaster at Cranbrook in November 1950, arriving in Australia in April 1951.</span></p>
  • <p><span style="font-size:15.5px;">At the beginning of Hewan's tenure there were 737 boys, of whom 552 were day boys and 185 were boarders.</span></p>
- Mr Mark Bishop -
1960 - 1969

Mark Bishop was appointed Headmaster in 1963. During this decade, the first issue of the Old Cranbrookian Magazine was published and the first stage of the Mansfield Building was opened. Woodward House was founded in 1968.

  • <p><span style="font-size:15.5px;">Mark Bishop started teaching science at Cranbrook in 1946, holding a number of positions throughout his tenure. In 1963, Bishop was appointed Headmaster, at which point there were 884 boys, of whom 712 were day boys and 172 were boarders. <a href="https://cranbrookcentenary.com.au/stories?tid=5"><strong>Learn more about Mark Bishop</strong></a>.</span></p>
- Mr Mark Bishop -
1970 - 1979

A busy decade under the continued leadership of Mark Bishop: the Senior School Building was built, the Junior School moved to the Perkins Building and boarders were relocated from 'Leura' to Harvey House. Hone House was established in 1970.

  • <p><span style="font-size:15.5px;">Cranbrook in the Field (CITF) was officially named during this decade. It is now compulsory for all Forms (1-4) to attend as part of the curriculum. <a href="https://cranbrookcentenary.com.au/stories?tid=6"><strong>Learn more about CITF</strong></a>.</span></p>
  • <p><span style="font-size:15.5px;"><a href="https://cranbrookcentenary.com.au/stories/108?tid=6"><strong>Learn more about our "Magnificent Three"</strong></a>.</span></p>
- Dr Bruce Carter -
1980 - 1989

Dr Bruce Carter began his leadership of the School in 1985 and the Student Council was formed. The Furber Building was opened and the first issue of The Chronicle was published. The iconic dark blue blazer was introduced as a regular part of the uniform. Cutler House was established in 1980.

  • <p><span style="font-size:15.5px;">In June 1985, Dr Bruce Carter was appointed Headmaster of Cranbrook School. At this time there were 1318 boys, of whom 1166 were day boys and 152 were boarders. <a href="https://cranbrookcentenary.com.au/stories?tid=7"><strong>Learn more about Bruce Carter</strong></a>.</span></p>
  • <p><span style="font-size:15.5px;"><a href="https://cranbrookcentenary.com.au/stories/112?tid=7"><strong>Learn more about Matt Street</strong></a>.</span></p>
- Dr Bruce Carter -
1990 - 1999

Under the continued direction of Dr Bruce Carter, the Furber Building was completed and the Perkins Building was converted to a music centre. Born in the Hour of Victory was published by David Thomas and Mark McAndrew, chronicling the life and times of Cranbrook School's first 75 years. Perkins House was established in 1994.

  • <p><span style="font-size:15.5px;"><em>"Born in the Hour of Victory"</em>,<em> </em>co-authored by David Thomas and Mark McAndrew, was commissioned by the School Council to celebrate and record 75 years of educational achievement.</span></p>
- Mr Jeremy Madin -
2000 - 2009

Under the direction of new Headmaster Mr Jeremy Madin, Cranbrook acquired the Rose Bay Bowling Club, the Prep School became known as the Cranbrook Junior School and construction began on the Kent Road campus. The Carter Centre was opened and the Felton Room was renovated as a staff common room.

In addition, Cranbrook built the Justin McDonald Stand (2004), refurbished the heritage-listed Rotunda (renamed the John Saunders Pavilion in 2006) and developed plans for the new Junior School campus at Rose Bay.

  • <p><span style="font-size:15.5px;">Jeremy Madin became Headmaster of Cranbrook School in 2001. In that year there were 1399 boys, of whom 1301 were day boys and 98 were boarders.</span></p>
  • <p><span style="font-size:15.5px;"><a href="https://cranbrookcentenary.com.au/stories/70?tid=9"><strong>Learn more about the 2003 Cranbrook Carnivale</strong></a>.</span></p>
- Mr Nicholas Sampson -
2010 - 2018

Current Headmaster since 2012, Mr Nicholas Sampson, makes his mark by purchasing land at Wolgan Valley and launching the Senior School Masterplan. The new Junior School campus opened its gates in 2012.

  • <p><span style="font-size:15.5px;">Nicholas Sampson became Headmaster of Cranbrook in 2012. Sampson has an ambitious vision for building on Cranbrook's strengths and values to create a blueprint for the future. In 2012, there were 1378 boys, of whom 1292 were day boys and 86 were boarders.</span></p>
  • <p><span style="font-size:15.5px;"><a href="https://cranbrookcentenary.com.au/stories/155?tid=10"><strong>Learn more about the Wolgan Valley property</strong></a>.</span></p>