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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.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A collection of photographs and architectural plans of the Music School since its opening in 1984.

A letter from the Headmaster Richard Bull to Parents regarding the Commemoration service, the Oakham School Young Masters, dressing code for School Photographs, the Quatercentenary Programme, the 1984 Appeal Raffle, the rule on tracksuits and second-hand uniform shop and guidelines on parties.

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 bound copy of several Old Oakhamian Magazines from 1980 to 1984.

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.

This file focusses on photographs of the Music School throughout the years.