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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.

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.

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

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.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

The Oakhamian Magazine, recording the Spring and Summer terms 1976. Contents: Editorial; School News; The School Council; Correspondence; Opinion; Societies; Music; Drama; The Chatty Catty Page; Jerwoods; Sport; R.A.F.; C.C.F.

The Oakhamian Magazine, recording the Summer term 1957 (published in Winter term 1957). Contents: School News; Avete; House Transfers; Valete; G.T.G.; C.C.F.; Shooting; Scout Notes; Cub Notes; Films; 21 Club; O.P.R.S.; Philatelic Society; Lectures; O.S.M.A.S.; The Last Frontier; Showtime; 19th Century School; Doctor in the South Pacific; Wild Man from Borneo; Toro; Swimming; Steeplechases; Cricket; Football; Excavations; O.O. News. Eleven double-pages A to K.

The Oakhamian Magazine, recording the Summer term 1960 (published in Winter term 1960). Contents: Editorial; School News; O.O. News; Avete; Land Utilisation Survey; The Weather Board; 1066 And All That; Land of the Midnight Sun; Societies; Music Notes; Literary; Combined Cadet Force; Waitwith Camp; Scout Notes; Games; Correspondence; Valete; Crossword. Twelve double-pages A to L.

The Oakhamian Magazine, recording the Spring term 1961 (published in Summer term 1961). Contents: Speech Day Sermon; School News; O.O. News; Avete; Retreat at Launde Abbey; Societies; Music Notes; Literary; North Wales Expedition; The Combined Cadet Force; Scout Notes; Games; Letters to the Editor; Valete; Contemporaries. Twelve double-pages A to L.

The Oakhamian Magazine, recording the Summerterm 1963 (published in Winter term 1963). Contents: President Kennedy; Editorial; School News; Avete; O.O. News; Treble Chance; Music; Societies; Face to Face no.3; Literary; We Pay our Respects to; The Combined Cadet Force; Scout Notes; Games; Problem Corner; Public Opinion Roll; Letters to the Editor; Valete. Fourteen double-pages A to N.