Jimmy started his career with a local amateur team Hamilton Central, and it was in 1913 when at a train station he was asked to play for Bolton Wanderers Reserves as they were a man short. He accepted the offer but despite playing 7 games for the club's first team that season and the next it was not until 1919 after the end of World War I despite contacting trench foot when serving during the war, that Jimmy signed for the club and became a professional.
Jimmy went on to have a long and prosperous career with the Wanderers playing 375 games in all completions, scoring 5 goals, he also collected 3 FA Cup Winners Medals in 1923, 1926 and 1929, captaining the team in the 1929 final. At the peak of his career Jimmy also picked up 6 caps for England, making his debut in 1923 against France in Paris.
Jimmy retired at the end of the 1931-32 season and went into coaching, he coached at Dordrecht in the Netherlands and Altrincham in the lower leagues before becoming Southport’s trainer in 1936. Jimmy retired from the game a few years later where he became manager of the Scarisbrick Hotel in Southport. He died in October 1971, aged 76.