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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 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 report from Rev John Darrall on the charity events organised during the Summer term 1993, including houses events, the Aerobathon and sponsored sporting challenges.

A poster advertising a non-uniform day intending to raise money for the Oakham Canal Green Corridor Project.

A poster advertising a non-uniform day raising money for a high school in Pokhara, Nepal.

This sub-series relates to events organised for visiting preparatory schools to Oakham School and promote the activities and various departments.

A salaries cash book, recording salary, payments, tax, and lunch for teaching staff, admin staff and matrons, from May 1963 to November 1965.

A bill sent by the Bursar to Lt. Col. J.H. Wright detailing the school fees for his two sons P.R. and R.K. Wright, including the inclusive fee due in advance for the coming term and some optional charges and extras for the past term.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

This collection focuses on major events that have occurred to the school and its pupils. This includes the Quatercentenary celebrations and the school's reaction to the COVID-19 pandemic.

The Quatercentenary celebrations compromised of several events including the visit to the school by Queen Elizabeth II and Prince Philip, Quatercentenary ball, and special productions to celebrate the recent opening of the Queen Elizabeth Theatre.

There is a detailed series on the school's Speech Day which includes a comprehensive list of programmes and award winners from the ceremony.

There is a excellent record of items showing how the school reacted to the COVID-19 pandemic. There is general communication to parents and staff, information on the structure of face to face and distance learning teaching, and also an illuminating collection of photographs taken by Ms. Fernandez in 2021.