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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.

Four pages (A to D) from a 1919 photo album, with captions below the photographs. Contents: Main entrance (School House), pupils after school fire, 1919; 'Tudor House' in Boughton; Rugby 1st XV, 1919; Burleigh gardens and pond; Old Hall and the quad; A cricket match; Lord French inspecting the cadets; St John's College; pupils in the quad; the Long Dormitory boys; a dog; Coates, 1919; pupils at the baths; Burleigh woods and hill; Market Place; F.C. Dwyer; Cricket 1st XI, 1919; The Rectory; C.F. Bayley.

This sub-series focusses on various photographs of the pupils and staff of School House as well as various documents related to the history of the house.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A photograph showing boys walking in the gardens leading to the Science block, with the Deanscroft Studies in the background, probably in the 1960s.

A note from Rod Smith explaining the process of applying for a desk in College House.

This sub-series focuses on various items related to the history of College House.

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

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 file focusses on reminiscences of life at Oakham School in the second half of the 19th century.