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Items are all photographs of the whole school, pupils and staff.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This sub-series focusses on photographs of various Chess tournaments and other events held at Oakham School.

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.

A collection of documents related to John Barber's book, "The Story of Oakham School". The sub-series includes photographs, letters received by the author, press cuttings advertising the publication and the book.