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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.

Bound Copy of several Old Oakhamian Issues; red and black, hard cover

A4 magazine, stapled; 12 pages; "2 Chairmen, 5 Headmasters and 4 new houses" headlines with various photographs of headmasters, girls and boys walking on campus on the cover; contents: All your Yesterdays, Oakham 1940-45, O.O. News, , Gardens & Grounds, Obituaries, Cricket World Trophy 1997