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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.

A photograph of the Headmaster Tony Little, Alan Grieve and David Woodcock, Head of Music. Date is unknown.

A group of two indexes (A and B) and negatives (C) of various photographs of the Headmaster Tony Little and a concert in Chapel. Date is unknown.

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 reviewing events of Spring term 2000. Contents: School rules; Music, Drama; Debating; Physics Olympiad; Sports achievements; Future dates.

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.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

An almost complete collection of the School's magazines dating from 1884.

The Oakhamian Magazine, recording the Summer term 1996. Contents: Farewells; History; Science; Miscellany; English; Languages; Art; Performing Arts; Sport; Houses; Miscellany.

The Oakhamian Magazine, recording the Winter term 1997. Contents: VIP Visitor; Gap Year; English; History; Community Service; Performing Arts; Art; Sports; Miscellany; Languages; Houses.