Sunningdale was founded in 1874 by Canon William Girdlestone. At that time it was a school for some thirty boys. In 1880 a Chapel was built and Canon Girdlestone was given special dispensation to conduct acts of worship in the School Chapel.

 In 1900 F.L. Crabtree took over as Headmaster and he was joined two years later by D.M. Smith who was joint Headmaster until 1924.

 In 1933 G.D. Fox became Headmaster. He was to do twenty years in the job. He did have five years away during the war, during which time he was awarded the Military Cross. Mr Crabtree held the reins in his absence.

 C.E.W. Sheepshanks was headmaster from 1953 to 1967. He and his wife Mary, who is a novelist, ran the school until twin brothers Nick and Tim Dawson acquired the school in 1967.

 The Dawson twins ran the school for 38 years during which time the school went from strength to strength. Tim's wife Prue was very involved in the domestic side of the school.

 In 2005, the current Headmaster, Tom Dawson took over and his wife Elisabeth is also heavily involved.