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This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

This file focusses on roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887.

A roll call for School House, Mr. Scriven's, Mr Williams' and the Day Boys in Spring term 1888.

A School list for the Autumn term 1911 organised from Form VI to Form I.

A School list for the Summer term 1932 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House and the Day Boys.

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 brown notebook recording the performance of candidates who took the entrance examination between 1970 and 1978.

This file consists of various registration books, since the 1960s.

A green hardback book containing lists of day boys for the Junior Entry and Sixth form entry, from September 1987 to September 1998.