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This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

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 edition of Matkin's almanack including a section on Oakham School on page 16.

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.

The Oakhamian Magazine, recording the Spring term 1966 (published in Summer term 1966). Contents: Editorial; School News; Avete; Term's Eye View; RFD, GRL, JM; Drama; Music; Around the Societies; Oakham Through the Looking Glass; Letter from America; Literary; We Pay our Respects to; Face to Face; The Combined Cadet Force; Arduous Training; Shooting; Scouts; Games; O.O. News; Valete.

A bound copy of several Old Oakhamian Magazines from 1953 to 1959.

A bound copy of several Oakhamian Magazines from 1964 to 1967. Item A has a black cover; item B has a brown cover.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

The Old Oakhamian Magazine, published in 1954. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; War Memorial Fund; O.O. Fund; Barraclough Hall; School News; O.O. Notes; Life in Kenya; Presidents of the Club; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Jobs for the (Old) Boys; Notices; Correspondence; Golf. Ten double-pages A to J.

The Old Oakhamian Magazine, published in 1966. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; School News; O.O. News; R.F.D.; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part I; Masonic Lodge; Notices; Correspondence; Diary Dates; Seven-a-Sides; Golf. Thirteen double-pages A to M.