This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

Oakham School Magazine, recording the Spring term 1924 (published in Summer term 1924). Contents: School Notes; Quinquennial Meeting of the Old Oakhamians; The New Classrooms and Laboratories at Wharflands; The Chapel; The Debating Society; The Cross Country Steeplechases; Cricket Fixtures and the Sports; Lectures; Dramatic Performances; O.T.C. Notes; Boxing; Fencing and Physical Training; Games Account - Balance Sheet for 1923. Five double-pages A to E.

Oakham School Magazine, recording the Winter term 1905 (published in Spring term 1906). Contents: Editorial; School Notes; Opening of the new school Buildings; Art and History in the East End; Football; Correspondence. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1913 (published in Summer term 1913). Contents: The New Buildings; School Notes; The Sports; The Debating Society; New Zealand; Montenegro as I saw it; Forest Life; Cricket Prospects for 1913; Football. Eight double-pages A to H.

Oakham School Magazine, recording the Summer term 1918 (published in Winter term 1918). Contents: Roll of Honour; School Notes; List of Old Oakhamians serving in the War - Corrections and Additions; Plan - School Buildings; A Letter from the Headmaster to Past and Present Members of Oakham School; Cricket; Correspondence. Five double-pages A to E.

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.

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

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.