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

The Old Oakhamian Magazine, published in September 1994. Contents: To Younger OOs and Others; Next Year's President; News & Announcements; O.O. News; Lives Remembered; School Sport; O.O. Sport; Diary Dates; Old Oakhamian Network.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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).

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 document written by Pam Baillie, Senior Mistress of Pocklington School, discussing the different attitudes to girls' sports in co-educational schools, staffing needed, facilities, and some solutions to foreseen issues. Three pages numbered A to C.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

This sub-file contains various photographs of Andy Wolstenholme, Rugby coach.

A storage file with negatives of Roger Blackmore's photographs. A list of contents: Les Cusworth, Medical Congress 1989, new buildings, Haywoods opening, Festival '89, athletics.

This series focuses on Round House pupils and staff since its opening in 1972 as the first purpose-built girls' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.