A photograph of nine boys, wearing sports caps. The photograph is from the early 1890s.

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

A collection of photographs of the School theatres, the Barraclough Hall and the QET.

A reprint of a photograph of the Church Passage with Oakham School boys.

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 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 various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.

Several loose leaf pages from a 1919 photo album including photographs of School House, 'after school fire' group, Tudor House Boughton, 1st XV, Burleigh ponds and 3 other views, Old Hall, Corner of dining room, School House quad, 'Pearse 120 not out' , Lord French inspecting OTC, St John's Cambridge, group in School House quad (very faded), Long Dormitory 1919, Munty (dog), Coates 1919, 'after a bathe' 1919 ; School House entrance and three various views, Market Place, swimming group, F.C.Dwyer, general view of Oakham, 1st XI cricket 1919 or 1920, and C.F.Bayley. Pages have cotton binding still attached. (scan 00388), (scan 00386), (scan 00383), (scan 00389), (scan 00384), (scan 00385)

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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.