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A photograph of the inscribed stone over the Old School door with a translation, and above is a photograph of the brass to the Founder in North Luffenham Church.

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 letter from Joanne Creighton, Foundation Director, to John Buckingham regarding Deanscroft's house photographs and names of the boys on those photographs.

A sermon preached by The Lord Bishop of Ossory, J.G.F. Day, on the occasion of the 350th anniversary of the Foundation of Oakham School.

Minutes of a Parent/Teacher Committee meeting held on 17 November 2001 in the Bowes Room (A). Contents: Apologies; Matters arising from the Minutes; Afternoon Activities; Oakham School Foundation; Security; Inspection; Term Dates; Timings of Parent/Teacher Meetings; Correspondence; Any Other Business; Representatives for Spring term 2002; Date of the next meeting. Enclosing a letter regarding road safety on Kilburn Road (B).

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.

An account of Oakham School with illustrations written by the Headmaster, Walter Lee Sargant in the early 20th century. Contents: Preface; Foundation and Old School; Curriculum and Examinations; Boarders and Houses; Notes on School Life; The Junior House.

A chronology of the school from its foundation in 1584 to 2016. Six pages numbered A to F.

A print out of a press cutting regarding school histories, including "The Story of Oakham School" by John Barber and "Operation Oakham" by John Buchanan.

A book compiling reproductions of rolls copy of the Charter of Oakham and Uppingham Schools and Hospitals from 1584 and attached is a letter dated from 19 November 1926 from Arthur Hawley to Walter Lee Sargant, sending the book to the school.