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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.

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.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.