His early career was interrupted by the First World War during which his left hand and forearm were shattered by enemy fire at Arras. He wore a glove to mask the withered hand and forearm for the rest of his life.[3][4]
Heart of Midlothian and Leeds City
Wilson debuted for Heart of Midlothian in January 1918, playing for them until the end of the following season. The Scottish League championship continued to be played during the conflict, and he scored 32 times in 33 official appearances.[5] He also played a handful of league matches for Hamilton Academical.[1]
He guested a couple of times for Leeds City in April 1918, scoring twice on his Peacocks debut at Bradford Park Avenue on 6 April.[6]
Dunfermline Athletic and return to Middlesbrough
In 1919 Wilson joined Dunfermline Athletic when they were part of the rebel Central League, a body outside Scottish Football League jurisdiction. When this league was absorbed by the SFL in 1921, those players previously contracted to a Scottish or English league side were obliged to return to whichever side held their registration as part of the agreement.
Thus Wilson returned to Middlesbrough in time for the 1921–22 season. He ended that season as not just 'Boro's top scorer but also the League's, with 31 strikes.[7]
Chelsea
In November 1923 Wilson joined David Calderhead's sizeable contingent of Scots at Chelsea mid-season for £6,500.[8] He was replaced at Middlesbrough the following month with Ian Dickson from Aston Villa for £3,000.[9] Wilson ended the 1923–24 season as both Middlesbrough and Chelsea's top scorer; both clubs were relegated from the top flight that season.
At Dunfermline and Middlesbrough, Wilson was capped 12 times by Scotland between 1920 and 1923; he averaged more than a goal per game with 13 goals. He scored another four in two unofficial wartime internationals.[11]
In 1934 he became Walsall manager. He then accepted a series of coaching positions, including at Chelsea, Gravesend and Northfleet, where he was the club's first manager following their formation in 1946.[4] He spent the 1946–47 season at Gravesend before departing.