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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.

The items in this series are books written and published by members of staff and are related to the history of Oakham School.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

Items are all photographs of the whole school, pupils and staff.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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.

This file relates to Jon Wills's time at Oakham School as a pupil and staff.