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).

A bound copy of several Oakhamian Magazines from 1942 to 1948.

This sub-series relates to Remembrance services held in the Chapel or other churches in Oakham.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2018 and Spring term 2019. Contents: Farewell to Headmaster Nigel Lashbrook; Academic; Performing Arts; Trips and Tours; Geography Trip to Morocco; Geography Trip to Iceland; Pastoral; Activities; Sport; Staff News; Old Oakhamian.

The Oakhamian Magazine, recording the Summer term 1939 (published in Winter term 1939). Contents: School News; The Library; The Museum; Quinquennial Festival - 1939; Debating Society; Music; Cricket v. Old Oakhamians; O.T.C.; Scouts; The First Six Weeks; Swimming Sports; Football; War List; O.O. News. Ten double-pages A to J.

The Oakhamian Magazine, recording the Spring term 1946 (published in Summer term 1946). Contents: Roll of Honour; Editorial; School News; J.T.C.; Scout Notes; Music Notes; J.C. Clark; Junior House Play; Boxing; The Sports; Junior Sports; Oakham School 50 Years Ago; Virgiliana; The Creation; As Others See Us; Cricket; O.O. News; O.O. Golfing Society; Football Fixtures; Correspondence. Item belonged to D.J. Stocks in Junior House. Nine double-pages A to I.

The Oakhamian Magazine, recording the Summer term 1940 (published in Winter term 1940). Contents: Roll of Honour; School News; Debating Society; Music Notes; J.T.C.; Scout Notes; Swimming Sports; Football; O.O. News. Item belonged to R.K. Sprigg. Six double-pages A to F.

The Oakhamian Magazine, recording the Winter term 1939 (published in Spring term 1940). Contents: Editorial; School News; Music; School Societies; O.T.C.; Scouts; Hockey; Cross Country Running; Rugby Football; O.O. News; War List; Roll Of Honour; The River Plate; Turkey at Easter; Cricket Fixtures. Item belonged to R.K. Sprigg. Six double-pages A to F.

The Oakhamian Magazine, recording the Spring term 1940 (published in Summer term 1940). Contents: Roll of Honour; Editorial; School Notes; Speech Day; Music; O.T.C.; Boxing; Sports; Cricket; O.O. News. Five double-pages A to E.