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This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

This series relates to the history of the Duke of Edinburgh's Award Scheme at Oakham School since 1973. Most of the collection focusses on the 1000th Gold Award celebrations in 2000 and the visit of Prince Philip.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

This series focuses on the School Choir. The oldest item dates from 1959.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This series gathers various correspondence regarding the Chapel throughout the years.

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 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 Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.