Dundee born left half Harry Matthew played for Forfashire and began his senior football career with Darlington in 1891 and joined First Division Bolton Wanderers the following year, making his Football League debut against Aston Villa that September, making 8 appearances for The Trotters before returning to Scotland to join Scottish League Dundee in 1893.
He then joined Southern League club Millwall Athletic in 1894, helping The Lions to finish as Southern League Champions in 1895 and 1896, finishing runners up in 1897, Matthew played twice for The Southern League against London while with Millwall, scoring 5 goals in 49 appearances for them before being transferred to Preston North End in May 1897. He made 19 appearances for The Lilywhites during 1897-98 before a return to the Southern League with Gravesend United in the 1898 close season.
He joined Irish League club Distillery in the summer of 1899 and while there he played for The Irish League in a 3-1 defeat to The Football League at Burnden Park, Bolton in November 1899. He returned to English football with Southern League Watford in January 1903, making 10 appearances for The Hornets before finishing with the professional game in the summer of 1903.