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A collection of documents relating to the Wilson Fields and cricket pavilion, including photographs of the opening. In 2005, the Springfield Playing Fields on Ashwell Road were renamed the Wilson Fields, to honour O.O. Lynn Wilson ('57). Lynn Wilson also funded the construction of a pavilion on the fields. The official opening ceremony took place on 16 May 2005.

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.

A collection of documents relating to the various Science buildings and laboratories on campus throughout the years. It includes the Sargant Laboratories and further refurbishments, the Biology block and the Mehra Faculty of Science. The bulk of the sub-series is made of architectural plans and designs.

Correspondence, both emails and letters, regarding a memoir on Gordon Sanderson and the memoir written by Niall Campbell, Gordon Sanderson's grandson.

This sub-series related to various conference and lectures organised at Oakham Schools and inviting other schools to attend.

This sub-series gathers programmes of recitals and concerts performed by the Oakham School Choir.

This sub-series focuses on the dedication of the Second World War memorial in the School Chapel in 1946.

This sub-series focuses on the rededication of the War Memorial Chapel in 2007. The refurbishment of the Chapel was largely due to the generosity of O.O. Brian A.F. Smith ('54). The service coincided with the opening of Littles house, an extension of Roun House, the Seventh Form girls' house.

This sub-series focuses on the history of the first Chapel organ, dedicated in 1930.

This sub-series relates to Carol services and other Christmas celebrations held in the School Chapel or in Peterborough Cathedral, over a period of several decades. The bulk of the sub-series focuses on the 2000s onwards.