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A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

This file contains various photographs of Chapel Close, including the main entrance through Market Place and the Reception building, throughout the years.

This sub-file focusses on photographs of the Barraclough Dining Hall since its construction in 1987.

Five photographs (A to E) of Roger Blackmore, Registrar, in Thailand at a British Boarding Schools stall, promoting Oakham School in 1996.

Two photographs (A and B) of the construction of the new Music School, next to the Barraclough Hall (theatre) as part of the Quatercentenary Development Campaign.

A brochure promoting the Quatercentenary Appeal. Contents: Change and Continuity; Achievements and developments-past & future; Appeal Objectives; The Way Ahead; How to Contribute.

A photograph of Rev John Darrall on Non-Uniform Day. Date is unknown.

A photograph of Roger Blackmore.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.