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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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 speech given by Headmaster John Buchanan on Speech Day addressing the boys, parents and staff. The speech is typed, with hand-written notations. Date is unknown, but estimated before co-education. Five pages A to E.

A speech given by Headmaster John Buchanan on Speech Day 1960, paying tribute to the Guest, Lord Carrington, discussing the move of his office, activities and boarding matters, Education in Rutland and the Crowther report. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1961, paying tribute to the Guest, Chairman of a Bank, discussingimprovements to facilities, the Headmasters' Conference, boarding matters, exam results and overview of the past year at School. The speech is typed, with hand-written notations. Seven pages A to G.

A speech given by Headmaster John Buchanan on Speech Day 1962, paying tribute to the Guest, Lady Barnett, discussing the past years events at School, the Duke of Edinburgh Award Scheme and Music at School. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1963, paying tribute to the Guest, Professor Day-Lewis, discussing the Direct Grant and school fees, Education in Rutland, expansion in numbers and improved facilities. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1969, discussing the the Independence, the Second Development Campaign, and the destruction of the cricket pavilion. The speech is typed, with hand-written notations. Five pages A to E.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.