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This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

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 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 file focusses on reminiscences of life at Oakham School in the second half of the 19th century.

A photograph showing boys walking in the gardens leading to the Science block, with the Deanscroft Studies in the background, probably in the 1960s.

This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.

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

The term fees for P. R. Wright and R. K. Wright including inclusive fees and optional charges.

This sub-series related to memorial services held in the School Chapel in memory of pupils, Old Oakhamians and staff members who passed away.

Several loose leaf pages from a 1919 photo album including photographs of School House, 'after school fire' group, Tudor House Boughton, 1st XV, Burleigh ponds and 3 other views, Old Hall, Corner of dining room, School House quad, 'Pearse 120 not out' , Lord French inspecting OTC, St John's Cambridge, group in School House quad (very faded), Long Dormitory 1919, Munty (dog), Coates 1919, 'after a bathe' 1919 ; School House entrance and three various views, Market Place, swimming group, F.C.Dwyer, general view of Oakham, 1st XI cricket 1919 or 1920, and C.F.Bayley. Pages have cotton binding still attached. (scan 00388), (scan 00386), (scan 00383), (scan 00389), (scan 00384), (scan 00385)