This file contains various items created by John Buchanan or relating to his headmastership (1958-1977).

A letter from the Headmaster Richard Bull to Parents regarding the Summer Activity Holidays, the Scholarship Examinations, the fees for music lessons, times for using the sports facilities, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the June meeting of the Finance Committee and School fees.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

A prospectus (A) promoting studying at Oakham School in 1935. Contents: Trustees; Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List. Enclosed are corrections to prospectus (B), and a form of application for admission (C).

A prospectus promoting studying at Oakham School in 1943. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; J.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Six double-pages A to F. Enclosed is a list of Trustees and Staff (G).

This file focusses on letters sent/received by G. Talbot Griffith.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

An account book recording pupils' fees from January 1925 to December 1931.

A photocopy of p.226 from an unidentified source regarding Dalton's comparative fees statistics for public schools in 1896.