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This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A note from the Personal Assistant to the Headmaster to Graham Smallbone regarding a message from Mr Ronald Dudley on the Court opening, the performance of the choir and Sir John Owen's grandfather attending Oakham School.

A letter from the Headmaster Graham Smallbone to Mr Justice Owen regarding his visiting the School and the Court opening, and his grandfather attending the School. Attached is a copy of the register with the entry for Arthur Wright. Two pages A and B.

A letter from the Headmaster Graham Smallbone to R.T. Constable-Maxwell, High Sheriff of Leicestershire, regarding the Court Opening in Oakham and providing the choir.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1996. Contents: Activities; Beef and BSE; Reports for Parents; Carol Service for Parents; Two Special Pleas; Changes of Staff. Two pages A and B.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1996. Contents: Drugs guideline; Events of the term; the Hospital Site.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1995, including the opening of the Library, the cricket season, the School inspection, exam results, fees, the Carol service and changes of staff.