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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.

An invitation card from the Headmaster and Mrs Lashbrook to the retirement dinner for Mr Jon Wills at Deanscroft on 21 June 2018.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This sub-file contains an almost complete group of Jon Wills' school reports from Form 3 to Form 7.

Order of service of the Thanksgiving service for the life of Oliver Richard Silvester Bull in Chapel on 23 January 2016.

A print-out of a photograph of Charlie Boland winning a cup on Sports Day in June 2006.

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.

Email correspondence regarding the staff leavers' farewells in 2009, organised by the Common Room. Three pages A to C.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2006. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.