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This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A group of four articles entitled the 'New light on Oakham History' by W.L. Sargant which were printed in a newspaper. The articles are based on research undertaken by Mr Sargant in the Muniment Room of Westminster Abbey and written whilst he lived in Sidmouth, therefore in the late 1940s-early 1950s. Four pages A to D.

This file focusses on artwork of various buildings on the School Campus in the 20th century.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

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.