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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 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.

Printed Powerpoint slides from a presentation on the centenary of Chapmans. Includes information on the school's founding, images of various school buildings from different times, campus maps and pupils; a history of Junior House/Chapmans House; and a list of Housemasters. Thirty-four pages A to AG.

A list of the Housemasters of School House from 1951 to 2001.

This sub-series focusses on the every day running of School House. The bulk of the sub-series is punishment books and record books from the 1950s and 1960s.

The School House beating book (A) recording punishment received by the boys between 1955 and 1966, when the Headmaster ended this form of punishment; also recording the prefects for each term. Enclosed is a letter (B) from John Barber to Graham Smallbone regarding handing the book over to the Archives.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

Order of service for the Dedication of the War Memorial in Chapel on 27 July 1946, in honour of the Old Boys who died in the Second World War. Three double-pages A to C.

This sub-series focuses on the dedication of the Second World War memorial in the School Chapel in 1946.