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A group of original photographs and print-outs used as illustrations in John Barber's "The Story of Oakham School".

A photograph of the opening of the Shakespeare Centre on 25 October 1969, used in John Barber's "The Story of Oakham School".

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.

The Oakhamian Magazine, recording the Winter term 1954 (published in Spring term 1955). Contents: School News; Avete; Valete; C.C.F.; Shooting; Scout Notes; Cub Notes; Chess; Debating Society; The Museum; Films; O.P.R.S. Notes; The Music Club; Lepidotus Elvensis; Sparks from the Torch; Oakham, Uppingham and St Olave's; She Stoops to Conquer; Easter Term Plays; American Schools and Other Things; Hockey; Under 14 Football; The Running Eight; Fives; Athletics Match; Boxing; O.O. News. Eight double-pages A to H.

The Oakhamian Magazine, recording the Spring and Summer terms 1975. Contents: Editorial; School News; Correspondence; Music; Drama; Societies; Games; C.C.F.; O.O. News; Valete; Avete.

The Oakhamian Magazine, recording the Summer term 1999. Contents: Editorial; OSCA; Speech Day; Chess; Drama; Music; French Trips; Leavers; Dublin; Duke of Edinburgh Award Scheme; A-Level Art & Design; Geography Expedition to Morocco; Corsica '99; House Reports; Sports; Oakham School 2050.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2018. Contents: News; Cover Story; Speech Day 2018; Lower School Prize Giving 2018; Features; Performing Arts; Trips and Tours; Pastoral; Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian.

The Old Oakhamian Magazine, published in 1956. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; Old Oakhamian Fund; Opening of the War Memorial Library; School News; O.O. Notes; Medals of Father Douglass; John Haywood; Engagements; Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Notices; Golf. Nine double-pages A to I.

This sub-file contains post cards related to the building and dedication of the War Memorial Chapel. Three post cards show the service of the laying of the foundation stone on Speech Day 1924. Four post cards show the dedication service on 29 October 1925. All post cards were published by Heawood & Son.