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This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

This file focusses on obituaries and tributes written in memory of former Headmaster, Richard Bull.

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

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.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

Correspondence relating to the Oakham School 1993 Development Plan.

This file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

Two notes from the Appeal Office to the Bursar (A) and the Headmaster (B), regarding the celebration of John Barber's birthday and the Barber Archive Room.

Notes from Graham Smallbone for the next Policy Meeting held on 21 October 1986, including comments on policies, school numbers, School campus and buildings, maintenance, OSEL and Appeals. Six pages A to F.

Four negatives of photographs of the Headmaster Graham Smallbone at a reception in Deanscroft and at Sports Day. Date is unknown.