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This series focusses on the history of Oakham School Politics Association, opened to pupils in the Upper School.

This sub-series focuses on the administration of Clipsham House.

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.

The Old Oakhamian Magazine, published in 1980. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Masonic Lodge; Notices; Diary Dates; Rugby Fixtures; Golf; Rifle Club; Letters; R.G.H.; Stop Press. Fifteen double-pages A to O.

The Old Oakhamian Magazine, published in 1981. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; T.C.S.H.; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Masonic Lodge; Notices; Diary Dates; Rugby Fixtures; Golf; Rifle Club; Letters; Stop Press. Seventeen double-pages A to Q.

A letter from Captain Paul Niemiec, Diocesan Youth Officer of the Diocese of Peterborough, to Rev Brian McAvoy, School Chaplain, thanking him for inviting him to the recent confirmation service.

A letter from Rev Rod Lee to Rev Brian McAvoy, School Chaplain, regarding the confirmation candidate Thomas Harris's attendance to church.

The Old Oakhamian Magazine, published in 1984. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; Oakham's Earliest Headmasters; A Breathing Space for Independent Schools?; North to the Future; Quatercentenary Appeal; Major Events 1984; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Golf; Rifle Club; Masonic Lodge; Notices; School Shop/Club Colours; Rugby Fixtures and Diary Dates; A Statistical History of Oakham School 1st XI Cricket; Centre Section - Oakham School Campus 1984. Eighteen double-pages A to R.

A bound copy of several Old Oakhamian Magazines from 1974 to 1979.

This sub-file contains two letters and Rugby School's Drugs Policies from the mid-1990s.