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This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

A letter from Alan Grieve to Roger Blackmore regarding the latest meeting of OSEL board.

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.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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.

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.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.

A letter from the Headmaster Richard Bull to Parents regarding the revised fees for the year 1980-1981.

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.

A letter from the Headmaster Richard Bull to Parents regarding the June meeting of the Finance Committee and School fees.