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 sub-file focusses on letters from Lord Winchelsea to Georgiana, relating to a cricket match between Dr Doncaster's boys and the County.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Dr John Doncaster.

Typed letters from Lord Winchelsea to Georgiana mentioning a cricket match between Dr Doncaster's boys and the County, and a post-match dinner. Three pages A to C.

This file focusses on letters sent or received by William Spicer Wood, Headmaster, in the mid-19th century.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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 letters and cards relating to Oakham School, sent/received under the headmastership of Rev Vere Hodge.

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.

A letter from Colin Edgar to Dr Joe Spence, Headmaster, enclosing "The Humf Letters".
"The Humf Letters" is a work by Colin Edgar, compiling letters sent by Lt. Douglas Herbert Washington Humfrey to Betty Dawes from the front during the First World War.