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A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Dr Leo Dudin as Deputy Head Academic in June 2018.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Arthur Mayhew as Senior Deputy Head in November 2018.

A letter from the Headmaster Henry Price to Parents regarding lockdown, and staff recruitment and changes.

A letter from the Headmaster Designate Henry Price to Parents regarding the reopening of the School for the Summer term 2021 and staff changes for the next term.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of James Robinson as Deputy Head Co-Curriculum in March 2021.

A letter from the Headmaster Henry Price to Parents regarding staff changes in the Upper School in January 2021.

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.

This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

A prospectus promoting studying at Oakham School in 1951. Contents: School History; Trustees and Staff; Curriculum; Boarding Houses; Clothes and Uniform; Health; Sports, Activities and Societies; Fees; Scholarships; Day Boys. Seven double-pages A to E. Enclosed is a list of staff (F).