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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.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

A collection of photographs and art work of Old School, oldest building of Oakham School, in Cutts Close park.

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

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 collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

A letter from Roger Blackmore to Alan Grieve regarding attending a meeting of delegates from companies marketing Activity Holidays and OSEL being represented in a sub-committee.

A letter from The Right Honourable the Lord Chalfont to the Headmaster Graham Smallbone regarding sending a copy of 'This War called Peace' to the School Library.

A letter from the Bursar Trevor Case to Michael Stevens regarding recommendations for Old School in 1985.