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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 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.

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 Summer term 2005. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; The Old Oakhamian; The Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

The Oakhamian Magazine, recording the Winter term 1975. Contents: School News; Correspondence; Drama; The Chatty Catty Page; Jerwoods; Sport; Avete; Valete.

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 1958 (published in Winter term 1958). Contents: School News; Avete; House Transfers; Valete; What is Toc H?; 21 Club; Chess; The Field Society; Stamp Club; The Band; O.P.R.S.; Lectures; O.S.M.A.S.; The Concert Club; Scout Notes; Film Notes; Showtime; Corps Notes; Bisley 1958; Problem Corner; Bert Cutting; The Brussels Exhibition; Rugger Forum; Trouble Brewing; Athletics; The Steeplechases; Swimming Sports; Cricket; Football; Hockey Fixtures; Correspondence; O.O. News. Eleven double-pages A to K.