"Bobbie" was initially turned down for the 1908 U. S. Olympic team; worked his way to Europe on a tramp steamer; and was accepted as an additional team member on the spot. Cloughen won the silver medal in the 200 m at the 1908 Summer Olympics in London. His preliminary heat time was 23.4 seconds; he dropped to 22.6 seconds to win his semifinal. In the final, Cloughen came from behind to nearly catch Robert Kerr on the straightaway; he lost by about nine inches as both finished in 22.6 seconds. Cloughen also competed in the 100 m in 1908, winning his first round heat with a time of 11.0 seconds before not starting in the semifinal round.