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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.

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.

The Oakhamian Magazine, recording the Winter term 1996. Contents: History; Gap Years; Art; Languages; Miscellany; English; Drama; Performing Arts; Sport; Science; Houses.

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

A photographic file recording three academic years, from 1996 to 2000. The photographs are the profile photographs of the girls, as well as formal and informal photographs of the Fifth and Sixth form girls. The photographs were initially gathered in a photo album.

A photograph of the Sixth Form girls and their Housemistress, Mary Hoyle, in Stevens house in the academic year 1995-1996. The photograph was taken by Brian and Elizabeth Nicholls Photography and the number of print is written on the back: JJ58/4.

The Oakhamian Magazine, recording the Spring term 1996. Contents: History; English; Performing Arts; C.C.F.; Science; Miscellany; Geography; Gap Year; Art; Sport; Houses; Miscellany.

A copy of the Common Room Club Registration Certificate, under Licensing Act 1964, section 40, signed by P.B. Hooper, Clerk to the Justices at Leicestershire Magistrates' Courts in 1996.

A photograph of the Sixth Form girls and their Housemistress, Mary Hoyle, in Stevens house in the academic year 1994-1995. The photograph was taken by Brian and Elizabeth Nicholls Photography and the number of print is written on the back: HH68/8.

An informal photograph of the Sixth Form girls in Stevens house in the academic year 1994-1995. The photograph was taken by Brian and Elizabeth Nicholls Photography and the number of print is written on the back: HH68/10.