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This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

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.

The Oakhamian Magazine, recording the Spring term 1942 (published in Summer term 1942). Contents: Roll of Honour; School News; Library; History Room; Speech Day; Music Notes; J.T.C.; A.T.C.; Scout Notes; Sports; Boxing; Cricket; O.O. Notes; Football Fixtures. Seven double-pages A to G.

The Old Oakhamian Magazine, published in Autumn 1998. Contents: Team of the Year; News of; Goodbye; Deanscroft/Haywoods 50th Anniversary; All Your Yesterdays; O.O. Sports; Obituaries; School Sport.

The Old Oakhamian Magazine, published in 1968. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; O.O. News; K.R.B.; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part III; Masonic Lodge; Notices; Diary Dates; Golf. Fourteen double-pages A to N.

A bound copy of several Old Oakhamian Magazines from 1968 to 1973.

This sub-series relates to the Scout Group of Oakham School. The bulk of the sub-series focusses on the 1930s.

The Old Oakhamian Magazine, published in 1976. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; J.W. and H.Y.H.; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Change of Address; Masonic Lodge; Notices; Diary Dates; Golf. Seventeen double-pages A to Q.

A bound copy of several Oakhamian Magazines from 1938 to 1943.