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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1995, including the opening of the Library, the cricket season, the School inspection, exam results, fees, the Carol service and changes of staff.

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.