Lancaster born outside left Norman Winn began his football career after the end of the First World War with hometown club Lancaster Town in 1919 and played for Morecambe in 1920 for whom he made 22 appearances before he was signed by First Division club Bradford City in May 1921, making his Football League debut against Burnley the same October. He scored twice in 25 appearances in his debut season but couldn’t help save The Bantams from relegation at the end of it. He spent three seasons at Valley Parade in and out of the team in the Second Division without scoring, before his best season for the club in 1925-26, when his eight goals in 26 appearances during the campaign ensured he was the club’s top scorer.
Described as “Not an orthodox forward but effective in so far as he ‘gets there’. Has skill as well as speed, appreciates the value of the open game shoots straight and with strength, An expert at manoeuvre and elusive in meeting a man”, Winn left Bradford City by the start of the following season to join Chorley after 10 goals in 91 appearances for The Bantams. He had further spells at Lancaster Town in 1927 and Morecambe in 1928 before eventually retiring from the game.