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This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools on 17 October 1971. Two pages A and B.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A book with the golden school crest on the cover compiling a selection from songs of Uppingham School composed and arranged by the Music-Masters of Uppingham School, with lyrics and music scores. The name 'Biggs' is hand-written on the first page.