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A prospectus promoting studying at Oakham School in 1937. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed are a form of application for admission (J) and a clothes list for the Junior House (K).

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

A storage file with negatives of Roger Blackmore's photographs. A list of contents: golf, Graham Smallbone, netball, the organ, cross country, Brisbane, football, hockey.

The Oakhamian Magazine, recording the Summer and Autumn terms 1981. Contents: Editorial; School News; Talbot Griffith; Religion; Prize winning Letter; Letters to the Editors; Profiles; Features; French Folies; Creative Writing; The Four Elements; Art & Design; Music; Drama; Societies; Ventures at Home & Abroad; Sport; University & Careers List.

This file focusses on photographs of G. Talbot Griffith, Headmaster of Oakham School.

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.

The Old Oakhamian Magazine, published in September 1991. Contents: The Bad News First; John Jerwood; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News Round-up; Staff; OSEL; Academic Results; Sporting Honours; Chapel; OSCA - Appeals Arrive Daily; Music; Drama; C.C.F.; DofE; O.S. Exploration Society; School Sport; When Life was Pretty Tough; Hardships of a Day Boy; Madness and Horror; Letters; New Members; Addresses of Members; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; O.O. Sport; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates.

The Old Oakhamian Magazine, published in Autumn 2000. Contents: The Torch in California; News of; London Dinner; Paris Dinner; Births, Marriages & Deaths; A Century of Sporting Achievement; Obituaries; 1000th Gold Award; All Our Yesterdays; Nursery School; The Millennium in Chapel.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.