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This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

A photograph of Father Douglass visiting the School in 1928. The photograph shows Father Douglass, Rev Scriven, Rev Edward Vere Hodge, Rev Frank Jerwood, Helen Hodge and Walter Lee Sargant in front of the Chapel.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A prospectus promoting studying at Oakham School in 1937. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed are a form of application for admission (J) and a clothes list for the Junior House (K).

Oakham School Magazine, recording the Spring term 1928 (published in Summer term 1928). Contents: School Notes; O.O. Club Notes; The Chapel Fund; Fives; The Sports; Sidney Sussex Run; Boxing and Fencing Club; O.T.C.; The School Register; To G.H.; Friday Music; Lectures; Cambridge Letter; Cricket; Correspondence; Games Balance Sheet. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1929 (published in Summer term 1929). Contents: Frontispiece; Editorial; School Notes; The Captain of the Ship; To G.H.; The Prefect's Lot; Extracts from a Wanderer's Diary; Boxing and Fencing Club; The Sports, Cricket; O.T.C.; O.O. News; Correspondence; Games Accounts. The name 'Worthington' is hand-written on the cover. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1930 (published in Summer term 1930). It is the 46th year of the Magazine. Contents: Frontispiece; Editorial; School Notes; The Sports; A Little Egyptian; Oakham School Players; The Debating Society; O.T.C.; Cricket; O.O. News; Games Account. The name 'Worthington' is hand-written on the cover. Eight double-pages A to H.

The Oakhamian Magazine, recording the Winter term 1931 (published in Spring term 1932). Contents: Editorial; School Notes; O.T.C.; Athletics; Football; Cricket Prospects; Society Notes; Strasbourg Cathedral; On Missing Tea; Spring; In the Clutches of the Foe; The New Boy who Won Through; Youth and Spring; The Call of the Sea; Lines to a Crafty Septuagenarian; Fog; A Country Cottage; On the Musical Propensities of VI Classical; Howlers; Answers to Correspondents; Cambridge Letter; O.O. News; Correspondence; Acknowledgements; Games Committee Balance Sheet. The initials 'T.H.W.' are hand-written on the cover. Ten double-pages A to J.

The Oakhamian Magazine, recording the Winter term 1932 (published in Spring term 1933). Contents: Editorial; School Notes; O.T.C.; Athletics; Football; Football Retrospect; The Duel; On Letter Writing; A Simple Story; The Victoria Falls; Gulliver among the Gol Fars; Scents; Action; Certificate Y Paper; Cargoes; Putting the Weight; Howlers; Cambridge Letter; Irish Cathedrals; O.O. News; Correspondence; Acknowledgements; Games Committee Balance Sheet. The name 'Worthington' is hand-written on the cover. Nine double-pages A to I.

The Oakhamian Magazine, recording the Winter term 1933 (published in Spring term 1934). Contents: Editorial; School Notes; School Officials; Avete and Valete; The Swimming Bath; The Chapel; The Library; Careers; End of Term Concert; Lectures; The Rivals; Debating Society; Philatelic Society; Reading Society; Photographic Society; Scout Notes; The Shepherds' Play; O.T.C.; Shooting Notes; Fives Notes; Athletics; Poems; The term's Howlers; A Banner with a Strange Device; Cambridge Letter; O.O. News; Correspondence; Acknowledgments; Games Committee Balance Sheet. Nine double-pages A to I.