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

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.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

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.

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.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

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.