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A photo album containing several photographs of the School buildings, including the interior of the Old School, the School House quad, a Physical Laboratory, The School House, School House dining hall and new changing rooms, Doncaster Close, the Gymnasium (now Queen Anne).

A prospectus promoting studying at Oakham School c.1909, with illustrations. Contents: Trustees & Staff; Brief History of the School; Subjects of Instruction; Upper School & Lower School; Boarding Houses; Health; Games; Holidays; Term's fees Scholarships and Exhibitions.

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 file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.