This file compiles reports and accounts of the Oakham School Charities Association since its inception in 1986 until 1999. The items give details on various charity events organised at school, on the charities and causes supported by the school and sums of money raised.

A headmaster's annual report for the academic year 1959-1960. Contents: Numbers; Staff; Activities; Health; Buildings and Grounds; Finance; General Remarks. Attached is a university awards report (appendix A). Nine pages A to I.

A headmaster's annual report for the academic year 1958-1959. Contents: Numbers; Staff; Activities; Health; Accommodation; Finance; General Remarks. Seven pages A to G.

A headmaster's annual report for the academic year 1957-1958. Contents: Numbers; Staff; Activities; Health; Accommodation; Finance; General Remarks. Twelve pages A to L.

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.