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This collection covers the charity and outreach work undertaken by Oakham School's staff and pupils.

There are sub-series focusing on OSCA (the school's charity association), the Rutland Water Walk, Voluntary Action, and interaction with local prep schools.

Photographic and administrative material are particularly dominant in this sub-fonds.

A poster advertise the Christmas Jumper Day to be held on 10 December 2021 at school in aid of Oakham's PHAB Group.

A programme for the Jerwoods Sports Day on 30 June 1999, including a list of events, the house teams, the 1998 results, the rules of competition and a list of the officials. Three double-pages A to C.

The items in this file are related to various events organised by the school in aid of charities.

A programme of the play 'The Thwarting of Baron Bolligrew' performed in the QET by Lower School pupils.

This sub-series is related to Oakham School's Voluntary Action and includes invitation, programmes, photographs and publicity on events organised by the pupils as their Service.

This sub-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.

This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.