Strathclyde, Glasgow born inside forward Matt Gillespie began his football career with Glasgow Thistle in 1891 and moved south to join First Division Blackburn Rovers in 1892, making his Football League debut against Accrington that October. He scored his only goal in 6 appearances for Rovers in a 2-2 draw with Derby County the following January, before joining Accrington for a brief spell in 1893. He returned to Scotland joining hometown club Strathclyde later the same year before a move to Leith Athletic in 1894.
He returned to Football League action when he joined Second Division Lincoln City with his younger brother in September 1895, scoring a hat-trick in Lincoln City’s record win, a 13-0 FA Cup romp at Peterborough Association that October, followed by successive hat-tricks in wins over Crewe Alexandra and Newcastle United immediately after Christmas. He finished as Lincoln’s leading goalscorer with 15 goals in the campaign, and he was signed by Newton Heath (now Manchester United) in November 1896 after 15 goals in 39 appearances for The Imps.
In his first season at Bank Street Newton Heath finished runners up in the Second Division and he played in four promotion Test matches which ultimately saw them lose out on promotion in a 3-1 aggregate defeat to Sunderland over two legs. They finished fourth in each of the next three seasons, and Gillespie played his final match for Newton Heath against Chesterfield in April 1900, before retiring from professional football.
He was the older brother of Billy Gillespie, who played with him at Lincoln City and had nine seasons at Manchester City, helping them to win the FA Cup in 1904.