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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 documents, mostly photographs, of the boarding house Haywoods on Kilburn Road, next to Chapmans. This new house was named after Colonel Tom Haywood, former Trustee. The boys previously in residence in Deanscroft moved into their new house in September 1989.

8 photographs of the opening of the Haywood Building

A collection of photographs used within J.L.Barber's The story of Oakham School.

A5 magazine, white cover with the badge of the school on the cover; 45 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Changes of Address, Masonic Lodge, Notices, Diary Dates, Golf, Stop Press; with a portrait of G.R. Snailham, a photograph of the Opening of Jerwoods, a photograph of Jerwoods and pupils walking