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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

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.

A4 magazine, stapled; 12 pages; "2 Chairmen, 5 Headmasters and 4 new houses" headlines with various photographs of headmasters, girls and boys walking on campus on the cover; contents: All your Yesterdays, Oakham 1940-45, O.O. News, , Gardens & Grounds, Obituaries, Cricket World Trophy 1997

A4 magazine, stapled; 12 pages; a letter from the Headmaster on the cover; contents: O.O. News, Obituaries, All Your Yesterdays, Oakham Memories, Sporting Highs, Oxford And Cambridge Places 1998

Bound Copy of several Old Oakhamian Issues; red and black, hard cover

Reminiscences of Jim O'Kane on his time working at Oakham School between 1973 and 2006. Four pages A to D.

A4 magazine, stapled; 12 pages; "Torch 2000" article on the cover; contents: O.O. News, News and Views, Indian World Cup, All Your Yesterdays, Sport & DofE News, Obituaries, Any Other Business