A right-handed batsman and right-arm slow-medium bowler, he was the older brother of Frank who had a more successful playing career, including representing England in 64 Tests.

Born in Tonbridge, Woolley began his cricket career with Kent however he failed to break into the first team, making 18 second XI appearances between 1906 and 1908.

[3] He joined Northamptonshire in 1911, making his debut for the club against the Indian tourists, he scored 1 not out batting at number 10 but did take his maiden first-class wicket, dismissing Mukundrao Pai.

[11] Woolley played 362 matches for Northamptonshire placing him eighth on the most appearances list,[12] and is the tenth highest scorer for the club with 15,353 runs.

[16] During a match between Warwickshire and Nottinghamshire in 1946 Woolley was temporarily required to officiate from both ends as fellow umpire George Beet was taken ill on the way to the game.