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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.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

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

Two letters from Janet Pickering, Senior Mistress of The King's School, Canterbury, regarding the minutes of the H.M.C. Co-Educational Senior Mistresses meeting held at Bristol Grammar School. Two pages numbered A and B.

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.

Two letters between Roger Blackmore and Alan Grieve on various matters, such as the last OSEL meeting, the new brochure for the Medical Congress and OSEL accounts.

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 Roger Blackmore to Alan Grieve regarding the latest minutes of OSEL meeting and discussing five points relating to catering.

A letter from Roger Blackmore to Alan Grieve regarding the minutes of an OSEL meeting and the publicity for the upcoming Chess Congress.