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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.

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 term 1958 (published in Summer term 1958). Contents: School News; Avete; House Transfers; Valete; Speech Day; Agamemnon; Problem Corner; A Study in Genius; The Lambeth Conference; Belfast Unmasked; Castle Excavations; 21 Club; O.S.M.A.S.; The Field Society; Philatelic Society; C.C.F.; Shooting; Scout Notes; Cricket; Cricket in Niue; Junior Sports; Football Fixtures; O.O. News. Nine double-pages A to I.

The Oakhamian Magazine, recording the Spring term 1959 (published in Summer term 1959). Contents: School News; Avete; House Transfers; Valete; Speech Day; The Sargant Laboratories; Music Notes; C.C.F. Notes; Shooting; Scout Notes; Football Fixtures; Cricket; Tennis; Problem Corner; O.O. News. Seven double-pages A to G.

The Oakhamian Magazine, recording the Spring term 1960 (published in Summer term 1960). Contents: Editorial; School News; O.O. News; Avete; Speech Day; Societies; Music Notes; Literary; Combined Cadet Force; Arduous Training Camp; Outward Bound; Scout Notes; Games; The Library; Contemporaries; Correspondence; Valete. Ten double-pages A to J.

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 Spring term 1963 (published in Summer term 1963). Contents: Editorial; School News; O.O. News; Avete; Speech Day; Societies; Music; Retreat - 1963; Comment; Face to Face no.2; Arduous Training 1963; The Combined Cadet Force; Scout Notes; Games; Letters to the Editor; Valete. Fourteen double-pages A to N.