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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This file focusses on admission prospectuses and various publications in the 1930s.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This sub-file focusses on photographs of the Barraclough Hall since its construction in 1946.

A collection of photographs of the Barraclough Hall since its construction in 1946. Once a warehouse at the terminus of the Canal on Ashwell Road, later converted into stables, the Barraclough Hall was named in honour of Mrs Barraclough, benefactor to the school, and in memory of her late husband, Norman Barraclough (OO, 1883). At the west end was the stage and the theatre would seat about three hundred and fifty people. Other features included a traditional long hall, raked stage and Proscenium Arch. The opening ceremony took place on 20 June 1953.

This sub-series contains various items related to Junior House/Chapmans. The bulk of the sub-series is informal photographs of everyday life in the boarding house in the 1950s/1960s.

This file focusses on material relating to Jon Wills' time at Oakham School as a pupil.

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

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Minutes of a meeting of the board of Oakham School Enterprises Limited held on 27 September 1983 in London. Contents: Activity Holidays Course Costings; Course Descriptions; Questionnaires; Chess Congress; Computer Courses; Date of the next meeting. With hand-written notes. Two pages A and B.