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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.

A copy of the Headmaster's address delivered in Chapel for the Seventh Form Leavers' service on 29 June 2007. Five pages A to E.

Order of service (A) for the memorial service celebrating the life of John David Buchanan, held in Chapel on 30 September 2005. Enclosed are a donation slip to a Memorial Bursary (B) and a blank tribute card (C).

Seven negatives of the opening ceremony of the Wilson Fields and Pavilion on 16 April 2005.

This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

Two photocopies of notes from Nigel J. Sudborough and Richard Hill congratulating the Headmaster Dr Joe Spence on a successful day at the C.C.F. Biennial Inspection and Reunion on 5 May 2006. Two pages A and B.

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 photocopy of four obituaries and death notices published in local newspapers in 2005 after the death of former Headmaster John Buchanan.

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