In his final year at Winchester, 1875–76, he was Prefect of Chapel, treasurer of the debating society, school fives champion, and opening bowler for the cricket team. In June 1876, he played cricket for the school team against Eton College, which won the match with a team including cricketing luminaries Ivo Bligh and Kynaston Studd, as well as a future Principal Private Secretary at the Home Office Evelyn Ruggles-Brise. Druitt bowled out Studd for four. With a glowing academic record, he was awarded a Winchester Scholarship to New College, Oxford.