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This sub-series focuses on photographs of boys in School House since the 1940s.

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.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

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 Winter term 1965 (published in Spring term 1966). Contents: Editorial; School News; Avete; Term's Eye View; College House; Drama; Music Notes; Opinion Poll; Saas Fee 1966; Geographical Field Study; Societies; English and Universities at Oakham; Literary; We Pay our Respects to; Games; The Combined Cadet Force; Letters to the Editor; O.O. News; Valete.

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

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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.