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A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

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.

A collection of documents relating to the Wharton pavilion, built on the site of the Old Gymnasium, adjacent to Wharflands. The opening ceremony took place on 4 July 1983 by O.O. Ron Jacobs ('45), President of the R.F.U. In July 2014, the Wharton Pavilion, known as Stumps, was taken down.

A letter from Robert Gregory congratulating John Barber on his book "The Story of Oakham School" and asking to be credited for his photograph.

The Oakhamian Magazine, recording the Spring term 1962 (published in Summer term 1962). Contents: Editorial; School News; O.O. News; Obituary; Avete; Pâques à Paris; Societies; Music; Literary; A Year at Oakham; The Combined Cadet Force; B.A.O.R. 1962; North Wales Report; Scout Notes; Games; Valete. Eleven double-pages A to K.

The Oakhamian Magazine, recording the Winter term 1966 (published in Spring term 1967). Contents: School News; Avete; Term's Eye View; Drama; Careers; Music; Saas Fee 1967; Around the Societies; Literary; We Pay our Respects to; Games; The Combined Cadet Force; O.O. News; Correspondence; Valete.