This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

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 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.

A book about the school including its history as well as contemporary daily life of the pupils.