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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

A letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the fees for music lessons, the scholarships, the Royal visit, and future term dates.

A letter from the Headmaster Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.

A letter from the Headmaster Tony Little to Nigel Richardson, Headmaster of the Perse School, regarding the Golden Jubilee and sending photographs of the Queen's visit in 1984.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A letter from the Headmaster Richard Bull and the Chairman of Trustees T.C.S. Haywood to Parents regarding the building of a new Biology Block, including plans, and the pre-payment of fees scheme III. Two pages A and B.

A letter from the Headmaster Richard Bull to Parents regarding the Parent/Teacher committee, talks on careers, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the Creative Arts in the Lower and Middle School, the influenza vaccination, the use Tippex and rules on Clothing.