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This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This sub-file focusses on two letters bet the Headmaster, John Buchanan, and O.O. Alwyne John Westmoreland ('32) regarding Oakham School winning the Ashburton Shield in 1966.

A letter from the Headmaster, John Buchanan, to O.O. Alwyne Westmoreland regarding Oakham School winning the Ashburton Shield in 1966.

A letter from O.O. Alwyne Westmoreland to the Headmaster, John Buchanan, regarding Oakham School winning the Ashburton Shield, captained by Chris Frame, in 1966.

A speech given by Headmaster John Buchanan on Speech Day 1964, paying tribute to the late Chairman, Sir Eric Gore-Browne, discussing three reports on Education, examination results, Music and other activities, sporting achievements, boarding matters and the Development Campaign. 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 1967, paying tribute to the Guest of Honour, Dr Hahn, discussing the Royal Visit, exam results and university successes, the Upper School innovations, shooting achievements, the Direct Grant and expansion of the School, K.R. Bowes's retirement. The speech is typed, with hand-written notations. Seven pages A to G.