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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 material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

A letter from Alan Grieve to Barry Turner at Hart Browne & Curtis Ltd regarding a possible press interview with John Jerwood.

Two letters between Roger Blackmore and Alan Grieve relating to a board meeting on 10 July 1984.

A letter from Alan Grieve to John Buchanan regarding the 1986 International Chess Tournament. Two pages A and B.

A letter from Alan Grieve to Roger Blackmore regarding the Easter Events, in particular the Business Studies DHD, Chess and the Engineering Course. Two pages A and B.

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

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

A photograph of Oakham School cadets being inspected on Doncaster Close. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157503.