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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 1910. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1910; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Seven double-pages A to G.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A School list of staff and pupils for the Summer term 1901. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1900; Oxford & Cambridge Board; Drawing Examination. Five double-pages A to E.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

Oakham School Magazine, recording the Winter term 1910 (published in Spring term 1911). Contents: School Notes; Officers' Training Corps; A Son of Empire; Mr. A.C. Johnson, Late Hereditary Trustee; The Concert; Rome; Wild Nature's Way; Caravan and Camera; Football; Correspondence. Seven double-pages A to G.

A book compiling the minutes of the Trustees' Financial Committee meetings.