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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.

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

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

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

School Magazine named "The Oakhamian - Winter 1994", stappled; a photograph of As You Like It on stage on the cover, 31 pages; contents: Farewells & Choir, Library, Houses, Lab-Oratory, Duesbury-Bowes Lecture, Art News, Performing Arts & Languages, Girls Sports, Sports Results, Boys Sports, Old School; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - February 1988", stappled; plain, burgundy cover wih yellow letters; 64 pages; contents: Editorial, People places events, J. Walton, The Chapel, Poem - Consideration, Speech Day, Into Industry, OSCA, Being New, Denis Giuseppi, The Ashburton, The Barraclough opening, Kenya, Drama, Poems, Sport, The Tramp, The Oxbridge Lie, Music, Societies and Travel, 20 years ago; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - May 1989", stappled; plain, brown cover with ornage letters; 56 pages; contents: Editorial, People Places Events, OSCA, Travel, Nostalgia, Societies, Music, Drama, Sport; with various photographs of staff, pupils, plays, sports, trips