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 file focusses on letter sent by Dr John Doncaster, Headmaster of Oakham School, regarding some pupils and staff matters. File dates from the first half of the 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.

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.

Book with a leather cover, containing fees for each term between Eater 1976 and Christmas 1879 with lists of parents/gardians' names, pupils' names, residence, age, fees for entrance, registration, tuition and lessons; with looses pages for receits

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 file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

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 file focusses on photographs dating from the second half of the 19th century, under the Headmasterships of Mr Tabraham and Rev Fitch.

This file focusses on reminiscences of life at Oakham School in the second half of the 19th century.