This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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.

The Oakhamian Magazine, recording the Summer term 1973 (published in Winter term 1973). Contents: School News; Correspondence; Drama; Music; Magic Mother's Problem Page; The Athelings Canadian Tour; Careers; Poetry; Games; C.C.F.; Scouts; Avete; Valete.

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.

A cash book recording pupils' fees and other charges on their school bills, from Summer term 1967 to Winter term 1970.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

A letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the fees for music lessons, the scholarships, the Royal visit, and future term dates.

A prospectus promoting studying at Oakham School in 1951. Contents: School History; Trustees and Staff; Curriculum; Boarding Houses; Clothes and Uniform; Health; Sports, Activities and Societies; Fees; Scholarships; Day Boys. Seven double-pages A to E. Enclosed is a list of staff (F).

A prospectus promoting studying at Oakham School in 1946. Contents: Foundation & History; The School today; Situation & Surroundings; Trustees; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, Deanscroft, The Junior House, Hodge Wing; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; J.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. Seven double-pages A to G. Enclosed are two trustees and staff lists (H and I) in 1946 and 1949.