Wilfred, the better-known competitor, made his debut at Wimbledon in 1889 and he went on to win singles title three times in 1891, 1892 and 1895.

[4] His 6–4, 1–6, 7–5, 6–0 win over Joshua Pim in 1891 at the age of 19 years and five months made him, until Boris Becker in 1985, the youngest men's singles champion at Wimbledon.

[4] The twins retired from competitive lawn tennis after the 1897 Wimbledon Championships to pursue their law careers but made a reappearance in the doubles event at Wimbledon in 1904 and 1905.

They joined their uncle and father Thomas and E. P. Baddeley in Leadenhall Street at the family firm, founded by their great-grandfather in 1790.

The brothers remained partners in the firm until 1919, when they retired leaving their cousin, Cyril Baddeley, to carry on in the family name.