Boston, Lincolnshire born inside right Dicky Leafe joined Second Division Grimsby Town from hometown club Boston Town on amateur forms in May 1909, making his Football League debut and sole Grimsby Town appearance against Stockport County that October. He returned to Boston Town at the end of the 1909-10 season before joining First Division Sheffield United in November 1911, making his debut for The Bladesagainst Liverpool in December, and scoring a hat-trick against Manchester United the following April in a 6-1 thumping. He got another hat-trick against Aston Villa in December 1912, but joined Southern League West Ham United May 1913 after 15 goals in 28 games for The Blades.
At West Ham he was the club’s top scorer in 1913-14 with 20 goals in 33 League games and he played both sides of the First World War, bagging 37 goals in the two seasons before the War, playing 15 matches in West Ham’s inaugural Football League season, although he didn’t feature in their inaugural fixture. By the time he played his final West Ham match in March 1922 he had scored 44 goals in 101 appearances. He decided to retire from playing in 1922 but was given the job as assistant secretary of the club. He held the post until the management was forced to reduce the staff at the outbreak of the Second World War.
His elder brother Tom also played for Boston Town as a half back and signed with him for Grimsby Town but never made an appearance for their first eleven.