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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.

This file relates to the National Youth Orchestra, in particular their newsletters in 1993 and 1994, and their stay at Oakham School in August 1993.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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 brochure promoting the Quatercentenary Appeal. Contents: Change and Continuity; Achievements and developments-past & future; Appeal Objectives; The Way Ahead; How to Contribute.

This file focusses on admission prospectuses and various publications in the 1930s.

This file focusses on writings by the Headmaster Nigel Lashbrook.

This file focusses on admission prospectuses published throughout G. Talbot Griffith's headmastership.

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.

This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.