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This sub-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series focuses on the Day girls' house of Hambleton, founded in 1997. The main items are informal photographs of house events and house diaries, planning and detailing the house routine throughout the years.

This sub-series focuses on the everyday running of Hambleton House. It contains reviews of the terms and the girls' achievements, as well as house accounts.

This file focusses on various documents relating to the history of the C.C.F. and the School Cadets, which do not fit in any other theme file.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

A brown account book recording deposits and entry fees for new pupils from 2000 to 2002.

This file contains account books recording deposits and entry fees for Junior Entry and Common Entrance, from 1978 to 2002, before recording on computer.