Starting out with Doncaster Rovers it would be at his next club, Sheffield United, where he enjoyed most success, playing in the top flight of English football.

[5] Despite making his first-class debut at the relatively late age of 25, Drake was a vital part of the Yorkshire team in the seasons before World War I. Drake started his career with Doncaster Rovers, for whom he made his Football League debut in 1902 but was soon bought by Sheffield United where he became a regular in the side for three seasons.

[2] Despite this he was viewed by some supporters as lazy with claims that he conceded possession too easily which led to regular barracking during games.

He grabbed 5/6 in the second innings against Derbyshire at Queen's Park, Chesterfield in 1914, including the wickets of Richard Baggallay, Gilbert Curgenven, Colin Hurt and Thomas Forrester in consecutive balls.

His most famous feat was the taking all ten Somerset wickets for 35 at Clarence Park, Weston-super-Mare in August 1914, when he took 15 in the match for 51 runs.