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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.

A document from Marsh & McLennan Companies regarding the insurance cover that parents can take out for their children.

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.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

Guidelines on the Tutorial system at Oakham School, presented to a staff seminar on 24 June 1986 by the Headmaster, Graham Smallbone. The paper discusses safeguarding and pastoral issues that might be encountered and mentions what is expected of a tutor and how they should behave. The four pages are numbered A to D.

Guidelines for Middle School Tutors, detailing their general responsibilities and their pastoral role at Oakham School. Two pages numbered A and B.

This sub-series contains School Rules from different years.

A list of the school rules and expectations for pupils including registration, the campus/town, lessons, rewards and sanctions, bullying, relationships, drugs, alcohol, smoking, uniform, Barraclough, transport, theft, weapons, suspensions, IT, mobile phones and complaints.