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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.

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

Old Oakhamian Calendar, published in 1924. Cover with contents: Editorial; List of Addresses of Members of the Old Oakhamian Club - 1924; Meeting of Old Oakhamian Club; Old Oakhamian Luncheon; A Letter from the Headmaster; Cambridge Letter; Officers' Training Corps; A Weekend in Africa; Births, Deaths and Marriages; Old Oakhamian Matches; School Staff - September 1924. Nine double-pages A to I.

Old Oakhamian Calendar, published in 1927. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members of the Old Oakhamian Club; Annual Dinners; Presentation to Mr J.C. Clark; The Headmaster's Letter; Cambridge Letter; Review of School Games, 1924-1927; Mr J.C. Clark's Trip to Canada; Births, Deaths and Marriages; Old Oakhamian Notes; Cricket and Football Matches; School Staff - September 1927. Thirteen double-pages A to M.

Old Oakhamian Calendar, published in 1930. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members; Annual Dinners; Headmaster's Letter; Mr J. Story's Letter; Quinquennial Luncheon and Meeting; Resignation of Mr W.L. Sargant - An Appreciation; The Captain of the Ship; Presentation to Mr W.L. Sargant; Cambridge Letter; The Book of Oakham School and The Register; Births, Marriages and Deaths; Cricket, Football and Shooting Matches; The Golfing Society; Club Notices; School Staff. Eighteen double-pages A to R.

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 series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

The Oakhamian Magazine, recording the Summer and Winter terms 1983. Contents: Editorial; School News; Departures; Features; Now and Then; Expeditions; Excursions; Travel and Adventure; Music Reports; Drama Reports; Society Reports; Staff at Play; Art and Design Activities; C.C.F.; Duke of Edinburgh Award and Estate Management Activities; Sport; University and Careers List.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.