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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.

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 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 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.

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 letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the Creative Arts in the Lower and Middle School, the influenza vaccination, the use Tippex and rules on Clothing.

A letter from the Headmaster Richard Bull to Parents regarding the Summer Activity Holidays, the Scholarship Examinations, the fees for music lessons, times for using the sports facilities, and future term dates.

This file focusses on newsletters, reviewing the terms' events and achievements.