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A note from the Headmaster Tony Little regarding the history of the school, its location, academic performance and co-curricular activities, sports, and school life.

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 Tony Little to Parents regarding a review of the Summer events, before the start of Winter term 1999. Contents: Timings of the first day of term; Expeditions; Maintenance work; Public Examination Results.

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 1996. Contents: Achievements in Drama, Music and Sports; Parent/Teacher Committee; Matters Academic; Building Development; Staff.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

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.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.