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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 fixture card for the 1984 season containing the fixtures for the 1st, 2nd, Colts XI (U16 and U15) and U14 and U13 cricket teams, as well as interhouse matches.

A fixture card for the 1989 season containing the fixtures for the 1st, 2nd, Colts XI (U16 and U15) and U14 and U13 cricket teams, as well as interhouse matches.

This sub-series focuses on photographs of girls, living in Stevens since its inception in 1989.

Internal email correspondence regarding the organisation of the first Christmas Party in 2005, discussing matters such as date, menu, venue, guest list, costs, and entertainment. Thirty-nine pages A to AM.

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 series focuses on Stevens House pupils and staff since its opening in 1989 after the conversion of Deanscroft, a former boys' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

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.