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This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2009. Contents: Staff News; Features; Trips and Events; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Old Oakhamian Magazine, published in 1986. Contents: Editorial; This Year's President; Annual Dinner; O.O. Day; Regional Reunions; O.O.'s Visited in Australia; An Aussie at Oakham; School News; O.O. News; New Members; Address Changes; Engagements, Marriages, Births & Deaths; Obituaries; Rifle Club; Masonic Lodge; Club Colours/School Shop; Notices; Rugby Fixtures; Diary Dates; Careers. Twenty double-pages A to T.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.

The Old Oakhamian Magazine, published in September 1994. Contents: To Younger OOs and Others; Next Year's President; News & Announcements; O.O. News; Lives Remembered; School Sport; O.O. Sport; Diary Dates; Old Oakhamian Network.

A bound copy of several Oakhamian Magazines from Spring 2009 to Summer 2011.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

The Old Oakhamian Magazine, published in 1987. Contents: A Very Good School; View From The Bridge; This Year's President; Annual Dinner; O.O. Day; Regional Reunions; School News - General; O.S.E.L.; Trevor and Sheila Case; Music; Drama; Attic Theatre Company; C.C.F.; Duke of Edinburgh Award Scheme; O.S.E.S.; Operation Raleigh; Kids come First; Round Britain Whizz; A Life of Undetected Crime; Sport; O.O. News; New Members; Address Changes; Engagements, Marriages, Births & Deaths; Obituaries; Our Oldest O.O.?; O.O. Golfing Society; O.O. Rifle Club; O.O. Lodge; Club Colours/School Shop; Notices; British P.S.A.; Victoria; A History of Oakham Rugby; Rugby Fixtures; Diary Dates; Careers Information. Twenty-one double-pages A to U.

A bound copy of several Oakhamian Magazines from Winter 1976 to Summer 1980.

The Old Oakhamian Magazine, published in 1985. Contents: Editorial; This Year's President; Richard Bull; O.O. Quatercentenary Dinner; A.G.M. and O.O. Day; Regional Reunions; 1984 - A Personal View; The Royal Visit; A Pilot through the Shoals; Life in the Twenties and the Eighties; School News; O.O. News; New Members; Address Changes; Engagements, Marriages, Births & Deaths; Obituaries; O.O. Golfing Society; O.O. Rifle Club; O.O. Masonic Lodge; Notices; Club Colours/School Shop; Rugby Fixtures; Diary Dates; Late News; An Oakham Overture to Poetry. Twenty-three double-pages A to W.