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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 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.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

An almost complete collection of the School's magazines dating from 1884.

The Oakhamian Magazine, recording the Winter term 1976. Contents: New Headmaster Appointed; Editorial; School News; O.O. News; Correspondence; Opinion; Drama; Music; Societies; Miscellany; Sport; C.C.F.; University/Careers List.

The Oakhamian Magazine, recording the Winter term 1977. Contents: Editorial; School News; Clubs and Societies; Drama; Music; Musing-Impressions-Travellers' Tales; Icelandic Summer; Japan; Summer retrospect; Sport; C.C.F.; School Council.

The Oakhamian Magazine, recording the Spring and Summer terms 1978. Contents: Editorial; School News; Co-Education - Seven Years On; A Guide to A Level Options; Civil Manoeuvres; Societies; The Arts; C.C.F.; Duke Of Edinburgh Award and Scouting Activities; Sport; The School Council.

The Oakhamian Magazine, recording the Winter term 1978. Contents: Editorial; School News; VOIR; Drama; Rutland Weekend Television Presents; Music; Clubs and Societies; Sport; The School Council.