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This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

The Old Oakhamian Magazine, published in Autumn 2002. Contents: Letter from the Editors; Dr joe Spence - Headmaster; '87 Reunion; Tony Little; O.O. Families' Day; Louise Doughty; The First One; Births, Marriages & Deaths; Three OOs in a Boat; Stars, Stripes and OOs; All Our Yesterdays; Obituaries; News of; Sport.

Order of service for the Service of Confirmation by the Right Reverend Ian Cundy, Bishop of Peterborough, held at the School Chapel on 6 May 2006, containing a list of those being confirmed.

Order of service for the Service of Confirmation by the Right Reverend Frank White, Bishop of Brixworth, held at the School Chapel on 5 May 2007, containing a list of those being confirmed.

This file contains orders of services and programmes for the school's Carol Services over the years.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

A collection of photographs relating to the Wilson Playing Fields and Pavilion, since its opening in 2005.

Print outs of the photographs of the rededication service of the Chapel and the opening of Littles house on 30 September 2007. Twenty three pages A to W.

Two photographs (A and B) of the Headmaster Joe Spence giving a speech at the opening ceremony of the Wilson pavilion. Also present was O.O. Lynn Wilson.