Drinkwater began his career at Athenian League club Hampstead in 1932 and failed to make an appearance before moving to Northfleet United in March 1933.
[6][7] Drinkwater's form earned him a move to Second Division club Brentford as an amateur in June 1934,[3] but he failed to make an appearance for the first team and returned to Golders Green for the start of the 1934–35 season.
[11] The Straits Times reported that Drinkwater "trapped a centre with the coolness of a veteran, steadied himself and drove the ball into the net".
[3] When competitive league play returned, Drinkwater made just one appearance during Watford's 1946–47 Third Division South season and he left Vicarage Road at the end of the campaign.
[3] After a spell training and coaching Pinner, Drinkwater resumed his playing career in April 1951, when he joined London League club Ruislip Manor as player-manager.