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A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 2001. Contents: Achievements in Music and Drama; Debating; Sports; International Baccalaureate; Staff; Road Safety; E-mail; Next term.

A programme for the visit of His Royal Highness The Duke of Edinburgh to Oakham School on 28 November 2000. Two double-pages A and B.

A photograph of Oakham School staff in 2002 under Headmaster Tony Little. The photograph is rolled and kept in its original green case.

The School photograph of 2000.

A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

A red photo album containing photos of several pupils an staff members, the Chapel, the Opening of Stumps and team photographs.

A booklet commemorating 30 years of Co-Education at Oakham School. Contents: message from John Buchanan, Up to 1970, the Concept of Co-Education, "There were a gallant lot", "For us, Co-Education is no an issue", "30 Years of Co-Education, highlights.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

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

A photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.