This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

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.