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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.

This series gathers various correspondence regarding the Chapel throughout the years.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.

This sub-series is made of various items, such as informal photographs of the girls in Ancaster, house events, house prefects and miscellaneous objects. The bulk of the sub-series focuses on the 2000s.

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 and The Old Oakhamian Magazine, recording the Spring term 2005. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; The Old Oakhamian; The Foundation.