Southport, Lancashire born centre half Jimmy Fay played local club football in Lancashire for Southport Crescent in 1900, Southport Blue Star in 1901, Southport Working Lads in 1902, and for Chorley in 1903 and Oswaldtwistle Rovers in 1904, before Second Division club Oldham Athletic signed him in May 1905. He made his Football League debut at Stoke in September 1907, playing his debut season at right half, and, after being tried at inside right in October 1901, top scored with 26 goals as they won promotion to the First Division in 1909-10, including scoring a hat-trick in March 1910 against Barnsley, although he subsequently reverted to mainly playing in the half back line in the top flight.
Two games into the 1911-12 season, having been ever present in four consecutive seasons for Oldham Athletic, he joined Bolton Wanderers after 37 goals in 164 appearances for The Latics. While with Bolton he played in four inter league games at centre half and was once reserve for England, and he played for Bolton both sides of the First World War, during which he played for Bolton in wartime league football and guested for hometown club Southport, but he returned to Burnden Park in 1919, eventually leaving in May 1921 to join hometown club Southport, already aged 37, as club captain after 5 goals in 136 appearances for The Trotters.. He stayed two seasons at Haig Avenue, where he scored twice in 29 appearances and played in their inaugural season in the Football League before retirement from the professional game in 1923, subsequently playing for non league Hesketh Park in 1923 before his eventual retirement.
He was one of the founders of the Player’s Union, of which he was Secretary and Treasurer from 1929 to 1955.