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A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Winter term 1991 to Spring term 2014.

A programme for the Oakham Fashion Show held in the Sports Hall on 18 March 2006 in aid of the Make-A-Wish Foundation.

A photo album containing several photographs of the School buildings, including the interior of the Old School, the School House quad, a Physical Laboratory, The School House, School House dining hall and new changing rooms, Doncaster Close, the Gymnasium (now Queen Anne).

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 series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A folder containing various documents on fundraising projects, the School's development plan; and examples of fundraising projects from other schools.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.