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This file consists of various entry books on potential future pupils.

A grille badge designed by Automotif Ltd for Oakham School. The item has a red and gold school crest in a glass window on a black, white and red background, in a metal frame; two screws at the bottom. The date is estimated between 2009 and 2017, when the company was in business.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

A wooden trophy made to look like a scroll with a large metal medallion in the centre and seven small ones, of which four are engraved with the wining house and year. The trophy was for the interhouse public speaking competition. The list of winners is as follows: Stevens in 1992; Haywoods in 1993; Buchanans in 1994 and 1995.

A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.