Monmore Green, Wolverhampton born goalkeeper Jimmy Massey began his football career in Yorkshire where he played for Denaby in 1888 and then Mexborough in 1889 before signing for Doncaster Rovers in 1890, who were then playing in the Midland Football Alliance League, and while at Doncaster he won the Sheffield and Hallamshire Senior Cup in 1891 and also made his debut in senior football playing in an FA Cup tie against Grimsby Town in October 1892.
He joined First Division Sheffield Wednesday in 1893, where he was initially understudy to Bill Allan, making his Football League debut against Aston Villa in November 1894, but he became the undisputed number one glovesman from February 1896 and played all 6 ties in what would prove the highlight of his career as Sheffield Wednesday marched to victory in the 1896 FA Cup Final, Wednesday beating Wolverhampton Wanderers 2-1 at The Crystal Palace.
He was an ever present in their 1896-97 campaign but was part of the Wednesday team that was relegated in 1899, however they bounced back immediately, winning the Second Division Championship in 1900 at the first time of asking. However he fell out of favour early in 1901 and his Wednesday career finished with Massey having made 173 appearances for The Owls.
In 1902 he returned to his original club Denaby United as an amateur whilst working at the local pit, he noted to the media at the time of joining Denaby that he had not played football for over two years. He continued playing for local clubs throughout the decade, including South Kirkby Colliery, Hickleton Main Colliery and Conisbrough St Peter’s until he lost an eye in a mining accident.
His grandson Roy Massey played League football as a centre forward for several clubs in the 1960’s.