Hurlford, Ayrshire born inside left Jack Picken began his career with Hurlford Thistle in 1897 before joining local professional side Kilmarnock in 1898. In the 1899 close season he moved to Second Division Bolton Wanderers, making his debut against Newton Heath in September 1899, soon establishing himself in the first eleven and helping Bolton to gain promotion in his debut season as Second Division runners up. He spent four years with the club, scoring 22 goals in 106 appearances for The Trotters.
When Bolton were relegated in 1903, Picken joined Southern League Plymouth Argyle that summer and was a great success during the club’s first two professional seasons, scoring 46 times in 90 appearances, including two hat-tricks in three games in October 1904 against New Brompton and Tottenham Hotspur. The Plymouth Argyle handbook of 1904-05 states “the good work this artist accomplished has been rightly esteemed and if he can obtain immunity from disaster even greater benefit will accrue to the club, spectators and player alike”.
Picken’s impressive goalscoring record brought him to the attention of Manchester United, for whom he signed in the 1905 close season. He scored 20 League goals in his debut season as United won promotion as Second Division runners up, and then helped United to two League Championships in 1908 and 1910 during his time with the club although he didn’t play in their 1909 FA Cup victory, scoring 46 goals in 122 appearances in all competitions. In the summer of 1911 he joined Burnley but found opportunities limited, scoring 10 goals in 19 games over two seasons at Turf Moor. He saw out his career with a further two year spell with Bristol City from 1913, scoring 14 goals in 54 games before the First World War effectively ended his career.