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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.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

This focusses on research done on Rev Edward Vere Hodge's headmastership, in particular teaching and support staff working then, and life at Oakham School in the late 19th century.

The Old Oakhamian Magazine, published in 1947. Contents: Editorial; Dedication of the War Memorial; Marriages, Births, Obituaries; War Memorial Fund; Golfing Society; O.O. Notes; Annual General Meeting; Old Oakhamian Fund; Notices. Two double-pages A and B.

A bound copy of several Oakhamian Magazines from 1938 to 1943.

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 bound copy of several Oakhamian Magazines from 1937 to 1941.