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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 blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

The Old Oakhamian Magazine, published in Autumn 1997. Contents: All Your Yesterdays; Oakham 1940-45; O.O. News; Gardens & Grounds; Marriages, Births & Deaths; Obituaries; Cricket World Trophy 1997.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.