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A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

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.

An email from Charles Welch to the Jerwood Housemasters regarding the results of Jerwoods interhouse competitions during the summer term, ahead of the Jerwoods Presentations in Assembly on 30 June 2004.

A certificate rewarding Oakham School's work to change the lives of formerly homeless people, signed by Mir Juma, Chief Excecutive.

A book (A) by Bryan Matthews, 'The Book of Rutland', given to Nigel Straton as a formal present for the Nelson Firth prize, awarded at Speech Day 1980 by the Headmaster Richard Bull. Enclosed is a letter (B) from Richard Bull to Nigel Straton; and a letter (C) from R.M. Chillery to the School, who found the book in a charity shop.

A War Certificate "A" awarded on 24 April 1944 to Cadet John David Witter who passed the examination on 21 March 1944.

A War Certificate 'A' awarded to cadet Anthony Jeffrey Doy of the Oakham School Contingent J.T.C. on 21 March 1945.

A Certificate 'A' awarded to cadet Philip Gordon Pearce-Smith of the Oakham School Contingent C.C.F. on 21 March 1949.