Boyle moved from his home in Scotland to join Sunderland in 1896, making his Football League debut against Blackburn Rovers in December of that year. After two years at the Wearside club he moved south to the League champions Sheffield United in December 1898 for £175. He became a regular for the "Blades" in a period when they were a dominant force in English football, finishing runners-up in the league in his first season and winning the FA Cup in both 1899 and 1902 along with another unsuccessful appearance in the 1901 FA Cup Final.