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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.

A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

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.