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An aerial photograph of Chapel Close, with High Street and Market Place in the foreground in 1937.

A photo album containing several photographs of the School buildings, including the interior of the Old School, the School House quad, a Physical Laboratory, The School House, School House dining hall and new changing rooms, Doncaster Close, the Gymnasium (now Queen Anne).

Four pages (A to D) from a 1919 photo album, with captions below the photographs. Contents: Main entrance (School House), pupils after school fire, 1919; 'Tudor House' in Boughton; Rugby 1st XV, 1919; Burleigh gardens and pond; Old Hall and the quad; A cricket match; Lord French inspecting the cadets; St John's College; pupils in the quad; the Long Dormitory boys; a dog; Coates, 1919; pupils at the baths; Burleigh woods and hill; Market Place; F.C. Dwyer; Cricket 1st XI, 1919; The Rectory; C.F. Bayley.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.

A greetings card with School House on front and unfinished message from L. Bowden Rectory to 'Dear Auntie' mentioning Bernard and skating on the canal in December 1901.

A print-out, probably from a school magazine, of Mrs Hassan's sketch of the Hospital of Christ in Oakham, on the site of the now School House in the 19th century, originally founded by Archdeacon Robert Johnson.

A drawing of School House quad, with pupils walking around, by Dennis Flanders for the Illustrated London News.

A drawing of School House from Market Street, by Dennis Flanders for the Illustrated London News.

A brochure of photographs of Oakham School buildings, probably in the early 1930s.

A photograph of John Story, teacher from 1891 to 1927, standing in School House quad, in front of the Fives court. Date is unknown.