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A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

A list of the String Ensemble members for the Winter term 2021.

Part of a prospectus promoting studying at Oakham School in 1929. Contents: Trustees & Staff; Brief History of the School.

A prospectus promoting studying at Oakham School in 1937. 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 are a form of application for admission (J) and a clothes list for the Junior House (K).

Notes by the Headmaster Graham Smallbone on the future needs of the School for a discussion in January 1986. Two pages A and B.

This file relates to reports about the School during Graham Smallbone's headmastership (1985-1996).

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.

A photograph of pupils on a boarders' trip to an adventure park in the Summer term 2021.

An A1 poster with photographs of six house events in the Spring term 2020: a boarders' trip to Laser tag; Rushebrookes' Junior Netball team competing in the 2020 Interhouse Netball competition; Quiz Night organised by the prefects; the Choir dinner; biscuit decorating; a Fifth form film night with Buchanans house.