Millom, Cumberland born inside or outside right Jimmy Settle was so fast paced that he could have chosen sprinting if he had not taken up football. He began his football career in junior football around the Bolton area before joining First Division Bolton Wanderers in 1894, making his Football League debut at Liverpool that September and scoring four times in 15 appearances for The Trotters in a single season before joining non league Halliwell Rovers in 1895. He returned to Football League action in January 1897 and scored 28 goals in 66 appearances for The Shakers before Everton signed him for £400 in April 1899. By then he had already won his first three England caps, scoring a hat-trick on his debut in a 13-2 thrashing of Ireland at Roker Park in February 1899 and scoring again in a 2-1 win over Scotland at Villa Park six weeks later.
He became club captain at Goodison Park, going on to win 3 more caps, scoring twice more, for England as well as playing in the void Ibrox Disaster match of April 1902, in which he also scored before the match was halted. He also represented The Football League on four occasions.
For Everton he was part of their teams that twice finished League runners up, in 1902 and 1905, and third twice in 1904 and 1907. Having been a member of the Everton team that lost the 1905 FA Cup semi final in a replay to Aston Villa, 2-1 at The City Ground, Nottingham, the following year he won the FA Cup with The Toffees when they beat Newcastle United 1-0 in the 1906 Final at The Crystal Palace, and was also a runner up a year later as Everton lost the 1907 Final 2-1 to Sheffield Wednesday. In May 1908 Settle was sold to Stockport County after 97 goals in 269 appearances for Everton, playing a single season for The Hatters, scoring twice in 29 appearances before his retirement in 1909.