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

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.

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

Correspondence relating to prospective major donors and contacting them about the 1993 Development Plan appeal.

Two photographs (A and B) of Charlie R and his parents, donating a framed England U18 rugby jersey.

Two photographs (A and B) of a pupil at the Leicestershire Cricket Academy signing a cricket bat as gift to the new Wilson pavilion.

Correspondence relating to the Oakham School 1993 Development Plan.

A brochure promoting the 1960s Development Campaign. Contents: Post war Development; The Development plan; The Cost; The Future; Administration of the Campaign; Method of Giving. Also inserted are a combined Deed of Covenant and Banker's Order form.

A list of Trustees, Old Oakhamians, Parents of present boys and Personal friends who raised the Sargant Presentation Fund in order that an organ might be placed in Oakham School Memorial Chapel. The book was presented to Walter Lee Sargant by Colonel Sir Herbert Bryan on 26 July 1930 when the organ was dedicated. Thirteen pages A to M.