A letter from Anne Rawlins to Parents informing them of two training sessions at Oakham RFC for their children before the Leicestershire Cross Country Championship at Braunstone Park in 1999.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This sub-series contains letters concerning Deanscroft house and pupils.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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

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 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.

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.

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

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.