New Delaval, Northumberland born outside right Jimmy Stephenson began his football career with New Delaval Villa before joining Aston Villa, initially on amateur forms in May 1913, turning professional in April 1914, his Football League debut coming at Everton in September 1914. He played both sides of the First World War for Aston Villa, 11 of his 32 appearances (he scored twice) coming before the suspension of peacetime football in May 1915, and during the conflict he also guested for Blyth Spartans and Leeds City. In May 1917, nearly three years since the outbreak of the First World War, Stephenson enlisted in the Royal Field Artillery and saw action on the Western Front and later served as part of the British Army of the Rhine.
However he remained a fringe player at Villa Park and didn’t play in their 1920 FA Cup Final triumph, and a year after Clem had left Villa Park for Huddersfield Town, he joined Sunderland for £2,000 in May 1921. A single season at Roker Park saw him score twice in 22 appearances before he joined Third Division (South) Watford for £500 in September 1922, where he was a virtually automatic choice throughout his five full seasons at Vicarage Road. During that time he scored 20 goals in 209 appearances for The Hornets, joining Queen’s Park Rangers on a free transfer in July 1927. He played 18 times for Rangers in the 1927-28 season before joining non league Boston Town, the predecessor of Boston United, in August 1928. He returned to New Delaval Villa in the close season of 1930 and briefly joined Ashington in December the same year, once again returning to New Delaval in February 1931.
Stephenson’s brothers were England international footballers Clem and George, both of whom played with him at Aston Villa, and he was the uncle of Bob Stephenson, who played for Derby County, Shrewsbury and Rochdale as well as being a first class cricketer with Derbyshire and Hampshire.