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A5 magazine, green cover; 63 pages; contents listed on the cover: Frontpiece, 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; with a photograph of Scriven, Douglass, Jerwood, Sragant, Hodge and Mrs Hodge

A5 magazine, green cover; 20 pages; contents listed on the cover: Editorial, The Old Oakhamian Club, Members of the Old Oakhamian Club 1898, Old Oakhamian Notes 1897-1898, The Old Oakhamian Dinner 1898, The Oakham School Register

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.

A programme for Speech Day service and the organ recital

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

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Items A to E

Staff and Trustees list and school roll per forms, including successes at the Royal Drawing Society Exam and Oxford and Cambridge examinations. Cover detached from the booklet. Items A to E

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

A roll call of the summer term including names of trustees, teachers, upper, middle and lower school, and prizes given out for subjects and awards. Items A to E

This sub-series contains various journals and reports of expeditions organised by Oakham School Exploration Society in the 1970s and 1990s.