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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.

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.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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

This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

This file contains invitations to various leavers/retirement events for staff.

A bound copy of several Oakhamian Magazines from Spring 2009 to Summer 2011.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2009 and Spring term 2010. Contents: Features; Staff News; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

A letter from Adam Lowe, a volunteer Special Constable with Leicestershire Constabulary, to Nigel Lashbrook, Headmaster of Oakham School, regarding a talk on Rutland County Police at the Rutland County Museum and research on the town prison.