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.

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 letter from the Headmaster Graham Smallbone to Parents regarding a review of the Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and B.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.

A certificate awarded to Gunthorpe House for winning the OSCA house shield or banner competition, judged by Jenny Little and Reverend John Darrall in 1998.

A photograph of Day girls showing their House banner, designed in 1998 as part of the House shield or banner competition organised by OSCA.

A group of print-outs of photographs of Rushebrookes' white party in the house garden, organised by the OSCA reps to support The British Heart Foundation in the Summer term 2022.

A print-out of a photographs of Rushebrookes' girls in the garden at the White party organised by the OSCA reps in Summer term 2022.

A print-out of a photographs of Rushebrookes' prefects in the garden at the White party organised by the OSCA reps in Summer term 2022.