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A letter from the Headmaster, John Buchanan, to Sandy Thompson regarding Oxbridge results in 1967 and holding a house for Nigel Webb in the Kilburn Yard.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

Two letters (A and B) to Roger Blackmore, new Chairman of the Holiday Lettings Committee, and to Nigel Webb, member of the Committee, regarding the new company and their new roles.

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 sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

A note from Nigel Webb, Second Master, regarding Derek Grant being in charge of the Shakespeare Centre.