Birmingham born winger Dickie York started his career with Handsworth Royal in 1914, playing for Birchfield Rangers in 1915 and then the Royal Air Force, and he also guested for Chelsea during World War One. He made 2 appearances for England Schoolboys prior to the War. In March 1915 he joined Aston Villa as an amateur, signing professional forms in August 1919, making his Football League debut at Sunderland that August in the opening post-war fixture. He scored one goal in 17 games in 1919-20, but did not feature in the 1920 FA Cup Final or any of the games leading up to it, which ended in a 1-0 victory over Huddersfield Town at Stamford Bridge. He appeared just 11 times in 1920-21, before establishing himself in the first eleven in 1921, going on to make 47 appearances in the 1921-22 campaign, as The Villa finished fifth in the First Division.
He won his first England cap at Villa Park in April 1922 when he played against Scotland in a match England lost 1-0. He also appeared at Wembley in the 1924 FA Cup Final, in a 2-0 defeat to Newcastle United. He scored 20 goals in 44 appearances in 1925-26 in what would be his career best season for goalscoring, including a hat-trick in a 3-2 win at Bury in October 1925. His form won him a recall to the England team but once again they went down 1-0 to Scotland in April 1926, this time at Old Trafford. He also made 2 appearances for The Football League. He was an ever present in 1926-27 and 1928-29, but by 1930 his days at Villa Park were numbered and he only appeared 4 times in the 1930-31 season when Villa finished League runners up.
He joined Port Vale in June 1931 with Arthur Dorrell for “a substantial fee” after 86 goals in 390 matches for Aston Villa, making his Vale debut in a 3-1 win at Plymouth Argyle on 29th August. He was a first team regular until he was struck by injury in December of that year. After his recovery he played infrequently, and ended the 1931-32 season with five goals in 26 Second Division appearances. He left The Old Recreation Ground and was transferred to Brierley Hill Alliance in August 1932.