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Items are all photographs of the whole school, pupils and staff.

This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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 is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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 is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

Photo albums and scrapbooks compiled by members of staff throughout the years.