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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.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

This file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

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 copy of the 1881 British Census for Oakham School, including names, ages, birthplaces, family and current addresses. Eight pages A to H.

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.

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 postcard from J.W.G. to G. Talbot Griffith on 25 October in the 1930s. The postcard shows School House and the Buttercross.

This file focusses on roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.