At the London Olympics in 1908 Barrett won a gold medal in the men's indoor doubles event with Arthur Gore. They also won the doubles in Wimbledon in 1909. In 1912 and 1913 he won the Wimbledon doubles title with Charles Dixon.
He played his first Wimbledon singles' competition in 1898, reaching the second round in which he lost to eventual finalist Lawrence Doherty. He achieved his best Wimbledon singles result in 1911 when he won the All-Comers final against compatriot Charles P. Dixon before losing in the Challenge Round to Anthony Wilding from New Zealand due to a retirement. Over the following years he would make regular appearances at Wimbledon until his final participation in 1921.
He participated in the first Davis Cup in 1900 and was the non-playing captain of the winning British Davis Cup team in 1933.
His most successful tournament wins were at the Suffolk Championships at Saxmundham which he won 17 times between 1898 and 1921.
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