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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.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

This file focusses on teaching staff photographs, since John Buchanan's headmastership. More recent photographs include both teaching and support staff.

This file focusses on various photographs of Richard Bull during his headmastership (1977-1984).

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.

A collection of documents relating to the Wharton pavilion, built on the site of the Old Gymnasium, adjacent to Wharflands. The opening ceremony took place on 4 July 1983 by O.O. Ron Jacobs ('45), President of the R.F.U. In July 2014, the Wharton Pavilion, known as Stumps, was taken down.

A collection of photographs of the Old Gymnasium and the Wharton Pavilion from the late 1970s.

This sub-file contains various photographs of Roger Blackmore, Teacher and later School Registrar.