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

A letter from O.O. J.A.S. Taylor to Brian Welford regarding his sporting career and some school memories; enclosed are photocopies of pages from Mr Taylor's scrapbook containing cuttings on his rugby career in the 1930s. Nine pages A to I.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

A bound copy of several Old Oakhamian Magazines from 1960 to 1967.

A bound copy of several Oakhamian Magazines from 1964 to 1967. Item A has a black cover; item B has a brown cover.

The Old Oakhamian Magazine, published in 1964. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; Development Campaign; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part IV; Notices; Golf. Fourteen double-pages A to N.

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 collection of photographs of the Old Gymnasium and the Wharton Pavilion from the late 1970s.

A bound copy of several Oakhamian Magazines from Winter 1980 to Winter 1983.