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This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

The items in this series are books written and published by members of staff and are related to the history of Oakham School.

This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

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 complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

This series relates to events organised by Oakham School Biology Society and the Medical Society.

This series focuses on the Day boys' house Barrow, founded in 1997. The main items are house photographs and handbooks.