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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus promoting studying at Oakham School in the 1930s. Contents: 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.

A letter from the Headmaster Richard Bull to Parents regarding the revised fees for the year 1980-1981.

A letter from the Headmaster Richard Bull to Parents regarding the fees for the year 1982-1983.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A prospectus promoting studying at Oakham School in 1942. 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; O.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. Nine double-pages A to I. Enclosed is modifications to the clothes list due to Rationing in July 1941 (J).

A letter from Headmaster G. Talbot Griffith to Mr J. Taylor regarding his son's entry to the Junior House in 1945.

A letter from Headmaster G. Talbot Griffith to Mr Atter regarding his son's possible entry in May, houses' full capacity and fees in 1943.