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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.

The Oakhamian Magazine, recording the Summer term 1930 (published in Winter term 1930). Contents: Frontispiece; Editorial; School Notes; Speech Day - Sargant Presentation; Upon Hearing Some Church Bells; Manhood; Cricket; Football, O.T.C.; Cambridge Letter; O.O. News; Correspondence; Acknowledgement. The name of the School Magazine was changed from 'Oakham School Magazine' to 'The Oakhamian'. The name 'Worthington' is hand-written on the cover. Nine double-pages A to I.

The Oakhamian Magazine, recording the Winter term 1994. Contents: Farewells & Choir; Library; Houses; Lab-Oratory; Duesbury-Bowes Lecture; Art News; Performing Arts & Languages; Girls Sports; Sports Results; Boys Sports; Old School.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

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.

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.

Oakham School Magazine, recording the Winter term 1909 (published in Spring term 1910). Contents: Editorial; School Notes; The Concert; Lectures; The Old School Frescoes; "Rondeau"; Football; Balance Sheet - Games Fund - 1909. Seven double-pages A to G.

A list of School buildings and their dates of construction and contractors compiled by R.E.M. Thomas, School Marshal, and other town buildings. Two pages A and B.

An aerial photograph of Chapel Close, with High Street in the foreground in 1937.

An aerial photograph of College House, the Chapel and School House, with High Street in the foreground in 1937.