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This series focuses on the School Choir. The oldest item dates from 1959.

The Old Oakhamian Magazine, published in September 1992. Contents: Annual Dinner - Revue 1992; A Special Place?; This Year's President; Annual Dinner 1991; O.O. Day and Reunions; School News - Round-up; Staff; Reminiscences of Oakham School 1960-1992; Admit Impediments? Twenty Years of Coeducation; Academic Results; Sporting Honours; Chapel; OSCA; Music; Drama; C.C.F.; Duke of Edinburgh's Award Scheme; O.S. Exploration Society; School Sport - Round up; O.S. Rugby Football 1892-1992; School Sports Reports; A Year in the Colony; Youngest ever Australian Senator; Commando Saved Life of Wounded Kurd; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; O.O. Sports - Round up; O.O. Lodge; Club Colours; Addresses of Members; Notices; Diary Dates.

This sub-series contains various informal photographs of the Day girls in Talbots throughout the years.

A bound copy of several Oakhamian Magazines from Spring 2005 to Winter 2006.

This file focusses on roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.

This file focusses on various items published under the headmastership of Rev Edward Vere Hodge in the late 19th century.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev Edward Vere Hodge.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.

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