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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.

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

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 Rt Hon William Hague MP to the Headmaster Tony Little, thanking him for the visit of the school and the opening of the Day houses.

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.

A letter (A) from O.O. Rakesh Mohan ('66) to the Headmaster Tony Little regarding his contribution to the QET seat appeal. Enclosed is Rakesh Mohan's C.V. (B to E).

A letter from the Headmaster Tony Little to Parents regarding a review of the Spring term 2001. Contents: Sporting achievements; Debating; Arts, Music and Drama; Mobile Phones; Pubs, Clubs and Alcohol; Match Day Information; Summer term events.

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.

Correspondence between O.O. Rakesh Mohan ('66) and the Headmaster Tony Little regarding the QET Seat Appeal in 1999.

Four letters, collated on one A3 sheet, addressed to the Headmaster Tony Little and Charles Welch, to thank them for various events such as the Harvest Party in 1997 and Oakham School's contribution to the Andrew Martin Trust.