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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.

Oakham School Magazine, recording the Spring term 1913 (published in Summer term 1913). Contents: The New Buildings; School Notes; The Sports; The Debating Society; New Zealand; Montenegro as I saw it; Forest Life; Cricket Prospects for 1913; Football. Eight double-pages A to H.

The Oakhamian Magazine, recording the Summer term 1970 (published in Winter term 1970). Contents: Editorial; School News; RSM D. Anderson; Correspondence; Term's Eye View; School House; Around the Societies; Drama; Music; Comment; Poetry; The Computer Terminal; The Library; The Creative Design Centre; Opinion Poll; Games; Shooting; Warcop - 1970; DofE Award Scheme; Avete; Valete.

Three black and white photographic book plates including the Hospital of Christ in Oakham, The School House, a transcription of the brass to the Founder and the inscribed stone over the Old School door.

Three photographs of Old School, All Saints Church and School House in their original frame. The photographs were taken by John Burton & Sons, Photographers and Artists, Leicester, in activity from 1863 to 1911.

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

A bound copy of several Old Oakhamian Magazines from 1960 to 1967.