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This series relates to the history of the Duke of Edinburgh's Award Scheme at Oakham School since 1973. Most of the collection focusses on the 1000th Gold Award celebrations in 2000 and the visit of Prince Philip.

Items are all photographs of the whole school, pupils and staff.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

This series focuses on the Millennium celebration which took place in the School Chapel, with an emphasis on the candelabras (objects and photographs) designed and made by the Art & Design Department for the special occasion.

This series focuses on various dedication and rededication services since the opening of the School Chapel. Most items are orders of services.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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.

An almost complete collection of the School's magazines dating from 1884.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..