He began his playing days with Arniston Rangers and signed for Hearts in August 1911 with Aniston team mate Paddy Crossan, but it was 19 April 1915 before he made his first team debut, against Leith Athletic in the semi-final of the East Scotland Cup. He scored twice in a 6-1 romp.

The following October he became the first Hearts player to score a hat trick against Rangers as the Edinburgh team won 4-0. With their line up in a constant state of flux, Hearts' form was patchy, but they could compete with the best on their day, as they proved when beating reigning champions Celtic 2-0 in November. At this point, Wilson (top scorer with 12 goals from 15 games) left to become a private in the Army, coinciding with Hearts' slide down the League.

At the end of February 1916, Wilson impressed when he turned out for a Scottish side in a military representative fixture at Elland Road. With Leeds City's regular centre-forward Jack Peart unavailable, Wilson was asked to fill the void on 4 March when the Peacocks played at Rochdale in the Subsidiary Tournament. He scored the second half goal that secured a 1-0 victory, cleverly controlling Jack Hampson's pass and sidestepping two or thee defenders before firing home left footed from outside the area.

The Leeds Mercury reported, 'Although Wilson scored the only goal of the match, he was sometimes at fault; he missed some really good openings.' Nevertheless, he retained his place for the home game with Bradford Park Avenue a week later, switching to his normal position on the left flank with Peart restored in the centre. He played well in a 3-2 victory, creating a couple of Clem Stephenson's three goals.

Wilson became a regular on the wing, scoring twice when City beat Rochdale 3-1 at Elland Road on 8 April, but after his battalion was moved further North a week later he missed a couple of games. He returned to play in the final two fixtures of the season, bringing his City total up to four from nine appearances when he scored in the 4-2 victory at Bradford City on the final day.

Wilson returned to Tynescastle after the Armistice, though he was constantly troubled by a shoulder injury after being wounded in action.

He remained at Hearts until 1922, signing off with a goal in his final appearance, a 3-1 win at home to Third Lanark on 21 January 1922.