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This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Includes some photographs of the school. Items A to H

A prespectus from this year including trustees and teaching staff names, information on the school, fees, and scholarships availible.

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Inside are a bookle on the rules of the Old Oakhamian Club and a membership slip. Items A to K

A prospectus including list of Trustees and staff. Contents: Subjects, Upper School, Lower School, Examinations, Boarding Houses, Library, Games, Extras, Terms, Holidays, Infectious disease, Scholarships, Exhibitions and Prizes. Items A to C

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes clothes list, rules for the Old Oakhamian club, programme for speech day, admission form and note regarding photographs. Items A to O

Part of a prospectus from that year which contains the names of staff and trustees, as well as the history of the school.

A prospectus' for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Includes some photographs of the school; with a list of corrections inserted and an admissions form. Items A to C