This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

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.

A fees book recording fees paid by pupils from Easter term 1876 to Christmas term 1879, including personal information such as parents' an guardians' names, addresses, age, entrance and registration fees and lessons chosen.

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.