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This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A headmaster's annual report for the academic year 1965-1966. Contents: Numbers; Staff; Activities; Health; Accommodation; Old Oakhamians; Circular 10/65; General. Attached are A-Level results (appendix A) and a report on conference 'Life in Industry' (appendix B). Thirteen pages A to M.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

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