Beesly received his BA in 1854 and proceeded MA in 1857. After failing to secure a first class (he obtained seconds in classical moderations and literae humaniores) or a fellowship, he became an assistant master at Marlborough College. His brother Augustus Henry, a historian and classical scholar, also taught at the school. Beesly left for London in 1859 to serve as principal of University Hall, a student residence in Gordon Square serving University College. The next year he was appointed professor of history there and professor of Latin at Bedford College for women, with a combined salary of £300. He also had a private income. His tall, willowy figure became a familiar sight in the Reform Club and London drawing-rooms, including that of George Eliot and George Henry Lewes, whose Fortnightly Review welcomed Beesly's articles.