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

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 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.

A bound copy of several Oakhamian Magazines from 1938 to 1943.

The Old Oakhamian Magazine, published in 1947. Contents: Editorial; Dedication of the War Memorial; Marriages, Births, Obituaries; War Memorial Fund; Golfing Society; O.O. Notes; Annual General Meeting; Old Oakhamian Fund; Notices. Two double-pages A and B.

The Old Oakhamian Magazine, published in 1990. Contents: Summer Ball; A Proud Record; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News - Round-up; Endings; The Chapel;£50,000 in Five Years; Music; Drama; The Oakham Festival; C.C.F.; Duke of Edinburgh and OSEL;, Sport; Jolly Hockey Sticks; Wharflands in the Thirties; Wharflands in the Forties; Whatever happened to; Public School Reminiscences; Letters; New Members; Addresses; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; O.O. Sport; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates.

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.

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.