Port Glasgow born inside right Hugh Bolton began his football career with Clydeville before joining Port Glasgow Athletic in 1902. After three seasons at Clune Park he was signed by First Division Newcastle United in May 1905, making his Football League debut, and only appearance for Newcastle, at Sheffield United in December 1905. He signed for Everton the following month, and played in their Cup run that led to his selection in the 1906 FA Cup Final at The Crystal Palace against his former club Newcastle United, with Everton triumphing 1-0 with a goal from Sandy Young.
In 1906-07 Bolton scored a hat-trick for Everton in a 5-1 win over Middlesbrough in December 1906 and then played in Everton’s FA Cup run that resulted in another FA Cup Final appearance at The Crystal Palace, albeit they were beaten 2-1 by Sheffield Wednesday. 1907-08 proved his best campaign for goalscoring while at Everton, Bolton scoring 15 goals, 4 of which came in an FA Cup Second Round replay win over Oldham Athletic, but he lost his place in September 1908 and signed for Second Division Bradford Park Avenue in December 1908 after 34 goals in 87 appearances for The Toffees.
He had two seasons at Park Avenue, scoring 7 goals in 30 appearances, before joining Greenock Morton in the 1910 close season. After three seasons at Cappielow, Bolton joined Irish League club Glentoran before returning to Scotland to play for Johnstone Burgh in 1916, his last club before his retirement.