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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.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

An almost complete collection of the School's magazines dating from 1884.

Oakham School Magazine, recording the Spring term 1928 (published in Summer term 1928). Contents: School Notes; O.O. Club Notes; The Chapel Fund; Fives; The Sports; Sidney Sussex Run; Boxing and Fencing Club; O.T.C.; The School Register; To G.H.; Friday Music; Lectures; Cambridge Letter; Cricket; Correspondence; Games Balance Sheet. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1928 (published in Winter term 1928). Contents: Editorial; School Notes; Speech Day; A Discontented Classic; Cricket; Informal Concert; O.T.C.; Mytchett Farm Camp 1928; O.O. Notes; Correspondence; Library; Acknowledgements. Nine double-pages A to I.

Oakham School Magazine, recording the Winter term 1928 (published in Spring term 1929). Contents: Frontispiece; Editorial; School Notes; The Concert; The Lamp of Life; The Prison Doors; Football; O.T.C.; The School Register; The Debating Society; O.O. News. The name 'T. Worthington' is hand-written on the cover. Eight double-pages A to H.