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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 series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

A group of negatives used as the illustrations in "The Story of Oakham School".

A brochure of photographs of Oakham School buildings, probably in the early 1930s.

This file focusses on publications, histories and articles, written by Walter Lee Sargant during his headmastership and his retirement. The items relate to the history of Oakham School and Oakham town.

An account of Oakham School with illustrations written by the Headmaster, Walter Lee Sargant in the early 20th century. Contents: Preface; Foundation and Old School; Curriculum and Examinations; Boarders and Houses; Notes on School Life; The Junior House.

An update to an earlier publication on the history of Oakham School, titled 'Thirty Years' Work' by W.L. Sargant in Easter 1908. It was printed for private circulation only. Three pages A to C.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A prospectus (A) promoting studying at Oakham School in 1935. Contents: Trustees; Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List. Enclosed are corrections to prospectus (B), and a form of application for admission (C).