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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.

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.

The Oakhamian Magazine, recording the Winter term 1954 (published in Spring term 1955). Contents: School News; Avete; Valete; C.C.F.; Shooting; Scout Notes; Cub Notes; Chess; Debating Society; The Museum; Films; O.P.R.S. Notes; The Music Club; Lepidotus Elvensis; Sparks from the Torch; Oakham, Uppingham and St Olave's; She Stoops to Conquer; Easter Term Plays; American Schools and Other Things; Hockey; Under 14 Football; The Running Eight; Fives; Athletics Match; Boxing; O.O. News. Eight double-pages A to H.

A bound copy of several Old Oakhamian Magazines from 1953 to 1959.

A bound copy of several Oakhamian Magazines from 1955 to 1959.

A letter from Margaret Kamester to Ms Hoare, Headmaster's Secretary, regarding information about the Old School frescoes and enclosing an entry for Mary Florence-Sargant.

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.

A letter from the Headmaster Graham Smallbone to O.O. James Fife regarding the debate concerning the frescoes in Old School.

A letter from the Headmaster Graham Smallbone to Dr Elizabeth Cumming regarding preserving the frescoes in Old School whilst trying to restore the historical building, and discussing the press coverage of the debate.

A bound copy of several Oakhamian Magazines from 1954 to 1959.