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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.

Minutes of a Parent/Teacher Committee meeting held on 25 October 1980 in Old Hall. Contents: Matters arising from the minutes; Role and Purpose of the School; Beginning and End of term dates; Any Other Business; Representation of the Committee; Date of the next meeting. Five pages A to E.

Minutes of a Parent/Teacher Committee meeting held on 7 March 1981 in Old Hall. Contents: Matters arising from the minutes; Any Other Business; Representation of the Committee; Date of the next meeting. Five pages A to E.

Minutes of a Parent/Teacher Committee meeting held on 21 November 1981 at the Headmaster's house. Contents: Matters arising from the minutes; Any Other Business; Representation of the Committee; Date of the next meeting. Three pages A to C.

Minutes of a Parent/Teacher Committee meeting held on 21 June 1981 in Old Hall. Contents: Matters arising from the minutes; Role and Purpose of the School; The Length of Exeats and Leave-Outs; Borrowing Equipment and Clothing; Any Other Business; Representation of the Committee; Date of the next meeting. Five pages A to E.

Minutes of a Parent/Teacher Committee meeting held on 15 May 1982 in Old Hall. Contents: Matters arising from the minutes; Quatercentenary Appeal; Possible Opportunities for Parents to meet the Headmaster; Entertaining prep schools and other visiting teams; Any Other Business; Representation of the Committee; Date of the next meeting. Two pages A to B.

Minutes of a Parent/Teacher Committee meeting held on 5 February 1983 in Old Hall. Contents: Matters arising from the minutes; Any Other Business; Representation of the Committee; Date of the next meeting. Four pages A to D.

Minutes of a Parent/Teacher Committee meeting held on 29 October 1983 in Old Hall. Contents: Matters arising from the minutes; Membership; Independent Schools action committee; Sub-Committee; Any Other Business; Representation of the Committee; Date of the next meeting. Four pages A to D.

Minutes of a Parent/Teacher Committee meeting held on 10 March 1984 in Old Hall. Contents: Matters arising from the minutes; Boarding/Day Accommodation; Sub-Committee on Parent/Teacher Activities; Times of Parent/Teacher Evenings; Any Other Business; Representation of the Committee; Date of the next meeting. Four pages A to D.