This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

This sub-series is related to the development of an Innovation Centre on the school campus and the Jerwood Sphere innovation day, involving teachers and Trustees.

A booklet produced by Davis Langdon & Everest for Oakham School on a first estimate for the Oakham Innovation Centre. Contents: Comparison between options, Summary of Estimate, List of drawings and other information, Exclusions, Schedule of Areas, Design Reserve and Contract Contingency, Inflation an Programme, Detailed analysis of construction costs.

An invitation from the Headmaster and Chairman of Trustees to a service of rededication of the School Chapel and to the opening of 'Littles' on 30 September 2007.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A letter from Richard Demarco to Graham and Dorothea Smallbone regarding his visiting the Queen Elizabeth Theatre and the performance of the Jerwood Players in 1995.

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.

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.

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 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.