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This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A list of School buildings and their dates of construction and contractors compiled by R.E.M. Thomas, School Marshal, and other town buildings. Two pages A and B.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

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.

An A1 poster with photographs of five house events in the Spring term 2020: a Fifth Form tutor outing to Wildwood in town after their mock exams; a Third form social with Buchanans; Rushebrookes Senior Netball team competing in the 2020 Interhouse Netball; Quiz night organised by the prefects; Rushebrookes girls on a paintballing trip at the weekend.

An A1 poster with photographs of three house events in the Spring term 2020: the Fourth Form going to a social; the Fifth Form girls having afternoon tea in town with their tutor; the house ready for the Easter egg hunt in Rushebrookes garden.

Four pages (A to D) from a 1919 photo album, with captions below the photographs. Contents: Main entrance (School House), pupils after school fire, 1919; 'Tudor House' in Boughton; Rugby 1st XV, 1919; Burleigh gardens and pond; Old Hall and the quad; A cricket match; Lord French inspecting the cadets; St John's College; pupils in the quad; the Long Dormitory boys; a dog; Coates, 1919; pupils at the baths; Burleigh woods and hill; Market Place; F.C. Dwyer; Cricket 1st XI, 1919; The Rectory; C.F. Bayley.

This file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.

This file contains various photographs of the boys in Sargants, mostly prefects groups, house families and year groups, in 1986 and in 1991.