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This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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.

A card from Charles Hawes to Jon Wills, donating the folder of photographs taken by Marshall, Keene and Co in 1937.

A letter from O.O. Conrad Garton ('58) to the Headmaster Dr Joe Spence thanking him for a successful C.C.F. Biennial Inspection and Reunion on 5 May 2006.

A bound copy of several Old Oakhamian Magazines from 1980 to 1984.

The Oakhamian Magazine, recording the Summer term 1934 (published in Winter term 1934). Contents: Editorial; School Notes; F.C.D.; The Chapel; The Library; Careers; The Photographic Club; Philatelic Society; Debating Society; Reading Society; Music Notes; Art; Scout Notes; O.T.C.; Cricket; Football; Swimming Sports; Golf Notes; Contributions; Cambridge Letter; London Letter; O.O. Notes; Acknowledgments. Nine double-pages A to I.

The Oakhamian Magazine, recording the Winter term 1935 (published in Spring term 1936). Contents: School News; School Concert; Reading Society; Debating Society; Photographic Society; The Library; Scout Notes; O.T.C.; Careers; Football; Athletics; Hockey; Very Modern Verse; Sparks from the Torch; Moderns' Lament; O.O. News; Correspondence. Seven double-pages A to G.

A letter from former Headmaster, G. Talbot Griffith, to O.O. Alan Jolly regarding gifts presented at a gathering and reminiscences of Alan Jolly's time at Oakham School.

A letter from the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.

A letter from Headmaster G. Talbot Griffith to Mr E. Clarke regarding his son, J.G. Clarke, having been accepted by Barclays Bank Limited as a Scholarship candidate and his entry to Oakham School in September 1950.