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An account book recording costs per pupil in the boarding houses and expenditures such as food, laundry, fuel and oil, gardens and general maintenance, from Autumn term 1949 to 1967.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.

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.

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 photograph of Stevens House, staff and pupils, in 1992-1993, with a house list stuck at the back. The photographs was owned by Rev Terence Treanor, a Tutor in Stevens.

An invitation from the Headmaster and Chairman of Trustees to a service of rededication of the School Chapel and to the opening of 'Littles' on 30 September 2007.

A photograph of Jon and Kim Wills as new Housemaster of Lincoln House in 1989.

A photograph of Jon and Kim Wills in front of Lincoln house, as new Housemaster in 1989.

This file relates to various School trips to the amusement park Alton Towers between 1999 and 2001.