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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

Old Oakhamian Calendar, published in 1913. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1913; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts.

The Oakhamian Magazine, recording the Summer term 1971 (published in Winter term 1971). Contents: School News; Term's Eye View; Around the Societies; Drama; Music; Careers; Poetry; Travellers' Tales; Games; Avete; Valete.

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 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 1930 (published in Spring term 1931). It is the 47th year of the School Magazine. Contents: Editorial; School Notes; Athletics; Football; Napoleon in our Midst; Our Village; Roots in the Soil; Motion; Requiem; The Study Wireless Set; O.T.C. Notes; Cambridge Letter; O.O. Notes; Acknowledgements; Correspondence; Games Committee - Balance Sheet for 1930. The name 'Worthington' is hand-written on the cover. Seven double-pages A to G.

The Oakhamian Magazine, recording the Spring term 1937 (published in Summer term 1937). Contents: School News; The Rev. F.H. and Mrs. Jerwood; Music; School Societies; Speech Day; Sports; O.T.C.; Boxing; Scouts; Bruges; Empire Rally of Youth; Swimming; Cricket; O.O. News; Correspondence. Item belonged to R.K. Sprigg. Eleven double-pages A to K.

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.

A blank post card showing the Dr Theodore Woods, Bishop of Winchester, laying the foundation stone on Speech Day, in 1924. The post card was published by Heawood & Son, Melton Mowbray and Oakham.

A blank post card showing the boys and staff gathered around the foundation stone on Speech Day in 1924, published by Heawood & Son, Melton Mowbray and Oakham.