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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).

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

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.

The Oakhamian Magazine, recording the Spring term 1998. Contents: Editorial; London Science Museum; R.A.F. Trip to Hunstanton; Study Visit to Berlin; Drama; Art & Design in Paris; Sports; Alzira exchange; Travel; Houses.

The Oakhamian Magazine, recording the Spring term 1999. Contents: Editorial; Chapel; OSCA; Oxbridge; Concerts; Inner Cities Project; Drama; The Battlefields; The Total Eclipse of the Sun; Russia; California; GCSE Design & Technology; Sports; Houses.