Dumbarton born right half Dickie Boyle began his football career with Dumbarton Episcopalians in 1885 and played for Dumbarton Union in 1886 and Methlan Park in 1887, before joining hometown professional game Dumbarton in 1888. He made his senior debut for Dumbarton in a 6-2 Scottish Cup win at Motherwell in October 1888 winning the first two The Scottish League Championships with The Sons in 1891 and 1892, also being part of Dumbarton’s 1891 Scottish Cup Final team that lost 1-0 to Heart of Midlothian at Hampden Park.
He won 2 representative caps for Dunbartonshire during the 1889-90 season and was a Scottish International trialist in 1892, without winning a full cap for Scotland. He did however represent The Scottish League in a 2-2 draw with The Football League at Pike’s Lane, Bolton in April 1892.
After 6 goals in 59 appearances for Dumbarton he joined First Division Everton in the 1892 close season, making his Football League debut against Nottingham Forest the same September, helping Everton to finish third in the League Championship and reach the 1893 FA Cup Final, where they lost to Wolverhampton Wanderers at Fallowfield, Manchester. A stalwart for Everton, he was an ever present in 1894-95 and 1895-96 as Everton finished as runners up and in third place in the League respectively, and in 1896-97 he missed only one match as Everton again reached the FA Cup Final, losing the Final to Double winners Aston Villa at The Crystal Palace, Boyle scoring a first half goal in their 3-2 defeat.
Boyle was again an ever present in Everton’s 1898-99 campaign, but lost his place after the end of the 1899-1900 season, remaining at Goodison Park for a further two seasons but making only 9 further appearances for The Toffees. He spent some time on loan with New Brighton Tower during 1901-02 before leaving Everton to return to Scotland with Dundee in the summer of 1902 after 8 goals in 250 appearances over ten seasons, an enormous number at the time when clubs played far fewer matches. Boyle continued to play for Dundee until his retirement in 1908, already aged 39, having scored 3 goals in 72 appearances for The Dark Blues.